CA1064048A - Process for the preparation of n-carbamoyloxy-phenyl-carbamates - Google Patents
Process for the preparation of n-carbamoyloxy-phenyl-carbamatesInfo
- Publication number
- CA1064048A CA1064048A CA231,284A CA231284A CA1064048A CA 1064048 A CA1064048 A CA 1064048A CA 231284 A CA231284 A CA 231284A CA 1064048 A CA1064048 A CA 1064048A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- alkyl
- carbamate
- phenyl
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 150000002148 esters Chemical class 0.000 claims abstract description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 7
- RDEOOHIDOFXZGU-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl)-phenylcarbamic acid Chemical compound ClC=1C(Cl)=C(Cl)C(Cl)=C(Cl)C=1N(C(=O)O)C1=CC=CC=C1 RDEOOHIDOFXZGU-UHFFFAOYSA-N 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 125000005270 trialkylamine group Chemical group 0.000 claims description 2
- LFXBHRAIYSPAOR-UHFFFAOYSA-N (3-methylphenyl)-(2,3,4,5,6-pentachlorophenyl)carbamic acid Chemical compound CC1=CC(=CC=C1)N(C2=C(C(=C(C(=C2Cl)Cl)Cl)Cl)Cl)C(=O)O LFXBHRAIYSPAOR-UHFFFAOYSA-N 0.000 claims 1
- KCLZXXMMEDEBMF-UHFFFAOYSA-N ethyl n-(3-hydroxyphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=CC(O)=C1 KCLZXXMMEDEBMF-UHFFFAOYSA-N 0.000 claims 1
- FFQQCJGNKKIRMD-UHFFFAOYSA-N methyl n-(3-hydroxyphenyl)carbamate Chemical compound COC(=O)NC1=CC=CC(O)=C1 FFQQCJGNKKIRMD-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 6
- -1 cyclopropyl cyclopentyl Chemical group 0.000 description 5
- SIZKDIQMNFWPBD-UHFFFAOYSA-N hydroxy(phenyl)carbamic acid Chemical compound OC(=O)N(O)C1=CC=CC=C1 SIZKDIQMNFWPBD-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 229940086542 triethylamine Drugs 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229940093499 ethyl acetate Drugs 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical class NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AURJXZJUNOGUEO-UHFFFAOYSA-N (2-carbamoyloxyphenyl)carbamic acid Chemical class NC(=O)OC1=CC=CC=C1NC(O)=O AURJXZJUNOGUEO-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
- MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical group C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 description 1
- 241001527806 Iti Species 0.000 description 1
- 230000006181 N-acylation Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000002989 phenols Chemical group 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/44—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI1490A HU170115B (es) | 1974-07-12 | 1974-07-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1064048A true CA1064048A (en) | 1979-10-09 |
Family
ID=10994526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA231,284A Expired CA1064048A (en) | 1974-07-12 | 1975-07-11 | Process for the preparation of n-carbamoyloxy-phenyl-carbamates |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS5132542A (es) |
| AR (1) | AR222621A1 (es) |
| BE (1) | BE831262A (es) |
| CA (1) | CA1064048A (es) |
| CH (1) | CH618584A5 (es) |
| CS (1) | CS194721B2 (es) |
| DD (1) | DD121512A2 (es) |
| DE (1) | DE2530521B2 (es) |
| DK (1) | DK139027B (es) |
| EG (1) | EG11800A (es) |
| ES (1) | ES439294A1 (es) |
| FI (1) | FI61873C (es) |
| FR (1) | FR2277816A1 (es) |
| GB (1) | GB1479250A (es) |
| HU (1) | HU170115B (es) |
| IL (1) | IL47668A (es) |
| IN (1) | IN140842B (es) |
| MX (1) | MX3678E (es) |
| NL (1) | NL7508245A (es) |
| NO (1) | NO752505L (es) |
| PL (1) | PL104534B1 (es) |
| SE (1) | SE420088B (es) |
| SU (1) | SU886738A3 (es) |
-
1974
- 1974-07-12 HU HUCI1490A patent/HU170115B/hu unknown
-
1975
- 1975-07-08 IL IL47668A patent/IL47668A/xx unknown
- 1975-07-09 EG EG401/75A patent/EG11800A/xx active
- 1975-07-09 DE DE2530521A patent/DE2530521B2/de not_active Ceased
- 1975-07-10 IN IN1349/CAL/1975A patent/IN140842B/en unknown
- 1975-07-10 FR FR7521688A patent/FR2277816A1/fr active Granted
- 1975-07-10 NL NL7508245A patent/NL7508245A/xx not_active Application Discontinuation
- 1975-07-10 FI FI752008A patent/FI61873C/fi not_active IP Right Cessation
- 1975-07-10 ES ES439294A patent/ES439294A1/es not_active Expired
- 1975-07-10 SE SE7507951A patent/SE420088B/xx unknown
- 1975-07-11 JP JP50084566A patent/JPS5132542A/ja active Pending
- 1975-07-11 DD DD187258A patent/DD121512A2/xx unknown
- 1975-07-11 BE BE158200A patent/BE831262A/xx not_active IP Right Cessation
- 1975-07-11 GB GB29290/75A patent/GB1479250A/en not_active Expired
- 1975-07-11 CS CS754932A patent/CS194721B2/cs unknown
- 1975-07-11 NO NO752505A patent/NO752505L/no unknown
- 1975-07-11 SU SU752153655A patent/SU886738A3/ru active
- 1975-07-11 CH CH912775A patent/CH618584A5/de not_active IP Right Cessation
- 1975-07-11 AR AR259528A patent/AR222621A1/es active
- 1975-07-11 DK DK318175AA patent/DK139027B/da not_active IP Right Cessation
- 1975-07-11 CA CA231,284A patent/CA1064048A/en not_active Expired
- 1975-07-12 PL PL1975182043A patent/PL104534B1/pl unknown
- 1975-07-14 MX MX75100304U patent/MX3678E/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL47668A (en) | 1978-03-10 |
| FI752008A (es) | 1976-01-13 |
| PL104534B1 (pl) | 1979-08-31 |
| HU170115B (es) | 1977-04-28 |
| FI61873C (fi) | 1982-10-11 |
| SU886738A3 (ru) | 1981-11-30 |
| DE2530521A1 (de) | 1976-01-29 |
| SE7507951L (sv) | 1976-01-13 |
| NL7508245A (nl) | 1976-01-14 |
| FR2277816A1 (fr) | 1976-02-06 |
| FR2277816B1 (es) | 1982-07-30 |
| BE831262A (fr) | 1975-11-03 |
| DE2530521B2 (de) | 1978-03-16 |
| CH618584A5 (en) | 1980-08-15 |
| IN140842B (es) | 1976-12-25 |
| FI61873B (fi) | 1982-06-30 |
| EG11800A (en) | 1979-03-31 |
| DD121512A2 (es) | 1976-08-05 |
| AR222621A1 (es) | 1981-06-15 |
| JPS5132542A (en) | 1976-03-19 |
| NO752505L (es) | 1976-01-13 |
| IL47668A0 (en) | 1975-10-15 |
| DK318175A (es) | 1976-01-13 |
| GB1479250A (en) | 1977-07-06 |
| SE420088B (sv) | 1981-09-14 |
| AU8296275A (en) | 1977-01-13 |
| ES439294A1 (es) | 1977-03-01 |
| MX3678E (es) | 1981-04-23 |
| DK139027C (es) | 1979-05-07 |
| CS194721B2 (en) | 1979-12-31 |
| DK139027B (da) | 1978-12-04 |
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