SU886738A3 - Способ получени N-(карбамоилоксифенил)-карбаматов - Google Patents

Способ получени N-(карбамоилоксифенил)-карбаматов Download PDF

Info

Publication number: SU886738A3
Authority: SU; USSR - Soviet Union
Prior art keywords: carbamic acid; mol; phenyl; general formula; ester
Prior art date: 1974-07-12

Application number

SU752153655A

Other languages

English (en)

Russian (ru)

Inventor

Тот Геза

Чабо Габор

Каллаи Тамаш

Хоффманн Дьердь

Original Assignee

Хиноин Дьедьсер Еш Ведьесети Термекек Дьяра Рт (Инопредприятие)

Priority date (The priority date 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 date listed.)

1974-07-12

Filing date

1975-07-11

Publication date

1981-11-30

1975-07-11 Application filed by Хиноин Дьедьсер Еш Ведьесети Термекек Дьяра Рт (Инопредприятие) filed Critical Хиноин Дьедьсер Еш Ведьесети Термекек Дьяра Рт (Инопредприятие)

1981-11-30 Application granted granted Critical

1981-11-30 Publication of SU886738A3 publication Critical patent/SU886738A3/ru

Links

238000000034 method Methods 0.000 title claims description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 32
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 20
239000011541 reaction mixture Substances 0.000 claims description 13
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 9
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 7
230000010933 acylation Effects 0.000 claims description 5
238000005917 acylation reaction Methods 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
-1 carbamoyloxy Chemical group 0.000 claims description 4
238000001816 cooling Methods 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
150000004657 carbamic acid derivatives Chemical class 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 2
150000001875 compounds Chemical class 0.000 abstract 3
239000013543 active substance Substances 0.000 abstract 1
230000002363 herbicidal effect Effects 0.000 abstract 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
FFQQCJGNKKIRMD-UHFFFAOYSA-N methyl n-(3-hydroxyphenyl)carbamate Chemical compound COC(=O)NC1=CC=CC(O)=C1 FFQQCJGNKKIRMD-UHFFFAOYSA-N 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
239000008096 xylene Substances 0.000 description 2
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 description 1
LCEYJTJDZROKOK-UHFFFAOYSA-N (3-hydroxyphenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC(O)=C1 LCEYJTJDZROKOK-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
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
241000357437 Mola Species 0.000 description 1
QJUIBXOTZQXQCO-UHFFFAOYSA-M NC([O-])=O.[Fe+] Chemical compound NC([O-])=O.[Fe+] QJUIBXOTZQXQCO-UHFFFAOYSA-M 0.000 description 1
101100471831 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) rpl-5 gene Proteins 0.000 description 1
244000062793 Sorghum vulgare Species 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical class C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
OQQXGCLLMDQESN-UHFFFAOYSA-N cyclohexylcarbamic acid Chemical compound OC(=O)NC1CCCCC1 OQQXGCLLMDQESN-UHFFFAOYSA-N 0.000 description 1
KCLZXXMMEDEBMF-UHFFFAOYSA-N ethyl n-(3-hydroxyphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=CC(O)=C1 KCLZXXMMEDEBMF-UHFFFAOYSA-N 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
SIZKDIQMNFWPBD-UHFFFAOYSA-N hydroxy(phenyl)carbamic acid Chemical compound OC(=O)N(O)C1=CC=CC=C1 SIZKDIQMNFWPBD-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
235000019713 millet Nutrition 0.000 description 1
BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
NBTQQBWMWTWDDG-UHFFFAOYSA-N phenyl carbamate;hydrochloride Chemical compound Cl.NC(=O)OC1=CC=CC=C1 NBTQQBWMWTWDDG-UHFFFAOYSA-N 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000011282 treatment Methods 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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)

SU752153655A 1974-07-12 1975-07-11 Способ получени N-(карбамоилоксифенил)-карбаматов SU886738A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HUCI1490A HU170115B (fr)	1974-07-12	1974-07-12

Publications (1)

Publication Number	Publication Date
SU886738A3 true SU886738A3 (ru)	1981-11-30

Family

ID=10994526

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU752153655A SU886738A3 (ru)	1974-07-12	1975-07-11	Способ получени N-(карбамоилоксифенил)-карбаматов

Country Status (23)

Country	Link
JP (1)	JPS5132542A (fr)
AR (1)	AR222621A1 (fr)
BE (1)	BE831262A (fr)
CA (1)	CA1064048A (fr)
CH (1)	CH618584A5 (fr)
CS (1)	CS194721B2 (fr)
DD (1)	DD121512A2 (fr)
DE (1)	DE2530521B2 (fr)
DK (1)	DK139027B (fr)
EG (1)	EG11800A (fr)
ES (1)	ES439294A1 (fr)
FI (1)	FI61873C (fr)
FR (1)	FR2277816A1 (fr)
GB (1)	GB1479250A (fr)
HU (1)	HU170115B (fr)
IL (1)	IL47668A (fr)
IN (1)	IN140842B (fr)
MX (1)	MX3678E (fr)
NL (1)	NL7508245A (fr)
NO (1)	NO752505L (fr)
PL (1)	PL104534B1 (fr)
SE (1)	SE420088B (fr)
SU (1)	SU886738A3 (fr)

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/fr 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/fr 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 (fr)	1976-01-13
PL104534B1 (pl)	1979-08-31
HU170115B (fr)	1977-04-28
FI61873C (fi)	1982-10-11
DE2530521A1 (de)	1976-01-29
SE7507951L (sv)	1976-01-13
NL7508245A (nl)	1976-01-14
FR2277816A1 (fr)	1976-02-06
FR2277816B1 (fr)	1982-07-30
BE831262A (fr)	1975-11-03
DE2530521B2 (de)	1978-03-16
CH618584A5 (en)	1980-08-15
IN140842B (fr)	1976-12-25
FI61873B (fi)	1982-06-30
EG11800A (en)	1979-03-31
DD121512A2 (fr)	1976-08-05
AR222621A1 (es)	1981-06-15
JPS5132542A (en)	1976-03-19
NO752505L (fr)	1976-01-13
IL47668A0 (en)	1975-10-15
DK318175A (fr)	1976-01-13
GB1479250A (en)	1977-07-06
SE420088B (sv)	1981-09-14
AU8296275A (en)	1977-01-13
ES439294A1 (es)	1977-03-01
CA1064048A (fr)	1979-10-09
MX3678E (es)	1981-04-23
DK139027C (fr)	1979-05-07
CS194721B2 (en)	1979-12-31
DK139027B (da)	1978-12-04

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