GB1080148A - Malonic acid monohydrazides - Google Patents
Malonic acid monohydrazidesInfo
- Publication number
- GB1080148A GB1080148A GB5132765A GB5132765A GB1080148A GB 1080148 A GB1080148 A GB 1080148A GB 5132765 A GB5132765 A GB 5132765A GB 5132765 A GB5132765 A GB 5132765A GB 1080148 A GB1080148 A GB 1080148A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- hydrazobenzene
- compounds
- prepared
- group
- 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
- VQFGMXGRVLYFPX-UHFFFAOYSA-N 3-hydrazinyl-3-oxopropanoic acid Chemical class NNC(=O)CC(O)=O VQFGMXGRVLYFPX-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 6
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical class NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 abstract 5
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- RRPMFPBYCATSMO-UHFFFAOYSA-N benzyl N-anilino-N-phenylcarbamate Chemical compound C=1C=CC=CC=1NN(C=1C=CC=CC=1)C(=O)OCC1=CC=CC=C1 RRPMFPBYCATSMO-UHFFFAOYSA-N 0.000 abstract 2
- -1 benzyl ester Chemical class 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 150000007529 inorganic bases Chemical class 0.000 abstract 2
- 150000007530 organic bases Chemical class 0.000 abstract 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 abstract 2
- JRWAEIMYVTVPFK-UHFFFAOYSA-N 2,2,2-trifluoro-N,N'-diphenylacetohydrazide Chemical compound FC(C(=O)N(NC1=CC=CC=C1)C1=CC=CC=C1)(F)F JRWAEIMYVTVPFK-UHFFFAOYSA-N 0.000 abstract 1
- FUSYZSFFEFFRQB-UHFFFAOYSA-N 2-phenylmethoxycarbonylhexanoic acid Chemical compound CCCCC(C(O)=O)C(=O)OCC1=CC=CC=C1 FUSYZSFFEFFRQB-UHFFFAOYSA-N 0.000 abstract 1
- CFLAHQSWDKNWPW-UHFFFAOYSA-N 3-(benzyloxy)-3-oxopropanoic acid Chemical compound OC(=O)CC(=O)OCC1=CC=CC=C1 CFLAHQSWDKNWPW-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- SSGVQJLNMKDNQN-UHFFFAOYSA-N CCCCC(C(O)=O)C(OCC1=CC=CC=C1)=O.Cl Chemical compound CCCCC(C(O)=O)C(OCC1=CC=CC=C1)=O.Cl SSGVQJLNMKDNQN-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- ZETNNJCANAUKGE-UHFFFAOYSA-N OC(CC(OCC1=CC=CC=C1)=O)=O.Cl Chemical class OC(CC(OCC1=CC=CC=C1)=O)=O.Cl ZETNNJCANAUKGE-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Catalysts (AREA)
Abstract
Compounds of the formula <FORM:1080148/C2/1> wherein R1 represents a hydrocarbon radical having at most 8 carbon atoms and R2 represents a hydrogen or halogen atom, and their salts with organic or inorganic bases, are prepared by (a) treating a compound of the formula <FORM:1080148/C2/2> wherein X represents a hydrogen atom or a benzyl group, with catalytically activated hydrogen until, depending on the meaning of X substantially the equinolar or double the equinolar amount of hydrogen has been taken up, or (b) treating a compound of the formula <FORM:1080148/C2/3> wherein Y represents a hydrogen atom or a benzyloxycarbonyl group and X represents hydrogen or a benzyl group, not more than one of X and Y being hydrogen, with sodium in liquid ammonia, or (c) treating a compound of the formula <FORM:1080148/C2/4> with at least two equivalents of an alkali metal or alkaline earth metal hydroxide and, if desired, the compound obtained by process (a), (b) or (c) is converted into a salt with an organic or inorganic base. Starting materials of the Formulae (II), (III) and (IV).-Compounds of the Formula (II) (wherein X is a benzyl group), compounds of the Formula (III) (wherein Y is a benzyloxy-carbonyl group and X is a benzyl group) and compounds of the Formula (IV) are prepared by reacting, in the presence of an acid-binding agent, an N-acylated hydrazobenzene of the formula <FORM:1080148/C2/5> wherein Ac represents a benzyloxycarbonyl or trifluoroacetyl group, with an a -substituted malonic acid benzyl ester chloride of the formula <FORM:1080148/C2/6> and when Ac is a trifluoroacetyl group hydrogenolysing the benzyl ester hydrazide. Compounds of the Formula (II) (wherein X is a hydrogen atom) and compounds of the Formula (III) (wherein X is a hydrogen atom and Y is a benzyloxycarbonyl group) are prepared by reacting a corresponding ethyl or methyl ester chloride instead of the benzyl ester chloride of Formula (VI) with an N-benzyloxycarbonyl hydrazobenzene and partially hydrolysing the ethyl or methyl ester hydrazide obtained with the equivalent amount of potassium or sodium hydroxide. Compounds of the Formula (III) (wherein X is a benzyl group and Y is a hydrogen atom) are prepared by condensing an appropriate malonic acid monobenzyl ester with hydrazobenzene or a dihalogenated hydrazobenzene N - Benzyloxycarbonyl hydrazobenzene is prepared by reacting hydrazobenzene with chloroformic acid benzyl ester. N-Trifluoroacetyl hydrazobenzene is prepared by reacting hydrazobenzene with trifluoroacetic acid anhydride. n-Butyl malonic acid benzyl ester chloride is prepared by reacting n-butyl malonic acid monobenzyl ester with thionyl chloride. Reference has been directed by the Comptroller to the Specification 1,022,010.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1574864A CH442345A (en) | 1964-12-04 | 1964-12-04 | Process for the preparation of new substituted malonic acid monohydrazides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1080148A true GB1080148A (en) | 1967-08-23 |
Family
ID=4411614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5132765A Expired GB1080148A (en) | 1964-12-04 | 1965-12-03 | Malonic acid monohydrazides |
Country Status (13)
| Country | Link |
|---|---|
| JP (3) | JPS5011369B1 (en) |
| AT (3) | AT260213B (en) |
| BE (1) | BE673288A (en) |
| BR (1) | BR6575426D0 (en) |
| CH (1) | CH442345A (en) |
| DE (1) | DE1493797C3 (en) |
| DK (1) | DK119501B (en) |
| ES (3) | ES320346A1 (en) |
| FI (1) | FI42090B (en) |
| FR (1) | FR1477465A (en) |
| GB (1) | GB1080148A (en) |
| NL (1) | NL6515772A (en) |
| SE (1) | SE314083B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5324160U (en) * | 1976-08-09 | 1978-03-01 | ||
| JPS53122276A (en) * | 1977-03-29 | 1978-10-25 | Gte Sylvania Inc | High power tungsten halogen lamp |
| JPS5571453U (en) * | 1978-11-09 | 1980-05-16 | ||
| GR67999B (en) * | 1979-05-11 | 1981-10-26 | Ciba Geigy Ag | |
| DE2919484C2 (en) * | 1979-05-15 | 1984-04-26 | Luco-Technic Gmbh Verfahrenstechnische Anlagen, 6474 Ortenberg | Device for wall cleaning using pressurized gas or steam |
| JP6095123B2 (en) * | 2014-06-18 | 2017-03-15 | 長谷川香料株式会社 | Process for producing alkyl-N-acetylglucosaminide |
-
1964
- 1964-12-04 CH CH1574864A patent/CH442345A/en unknown
-
1965
- 1965-12-03 AT AT232567A patent/AT260213B/en active
- 1965-12-03 JP JP7393865A patent/JPS5011369B1/ja active Pending
- 1965-12-03 AT AT1090065A patent/AT260212B/en active
- 1965-12-03 ES ES0320346A patent/ES320346A1/en not_active Expired
- 1965-12-03 SE SE15668/65A patent/SE314083B/xx unknown
- 1965-12-03 FR FR40895A patent/FR1477465A/en not_active Expired
- 1965-12-03 FI FI292265A patent/FI42090B/fi active
- 1965-12-03 GB GB5132765A patent/GB1080148A/en not_active Expired
- 1965-12-03 DE DE19651493797 patent/DE1493797C3/en not_active Expired
- 1965-12-03 ES ES0320347A patent/ES320347A1/en not_active Expired
- 1965-12-03 BR BR17542665A patent/BR6575426D0/en unknown
- 1965-12-03 BE BE673288D patent/BE673288A/xx unknown
- 1965-12-03 AT AT232667A patent/AT260214B/en active
- 1965-12-03 ES ES0320345A patent/ES320345A1/en not_active Expired
- 1965-12-03 NL NL6515772A patent/NL6515772A/xx unknown
- 1965-12-03 DK DK624265A patent/DK119501B/en unknown
-
1967
- 1967-01-28 JP JP528667A patent/JPS5011370B1/ja active Pending
- 1967-01-28 JP JP528767A patent/JPS5015780B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE1493797A1 (en) | 1969-08-07 |
| AT260213B (en) | 1968-02-12 |
| NL6515772A (en) | 1966-06-06 |
| BR6575426D0 (en) | 1973-09-06 |
| BE673288A (en) | 1966-06-03 |
| SE314083B (en) | 1969-09-01 |
| ES320346A1 (en) | 1966-06-01 |
| JPS5015780B1 (en) | 1975-06-07 |
| ES320347A1 (en) | 1966-06-01 |
| AT260214B (en) | 1968-02-12 |
| ES320345A1 (en) | 1966-06-01 |
| JPS5011370B1 (en) | 1975-04-30 |
| DK119501B (en) | 1971-01-18 |
| JPS5011369B1 (en) | 1975-04-30 |
| FR1477465A (en) | 1967-04-21 |
| DE1493797C3 (en) | 1975-02-13 |
| CH442345A (en) | 1967-08-31 |
| AT260212B (en) | 1968-02-12 |
| DE1493797B2 (en) | 1974-06-27 |
| FI42090B (en) | 1970-02-02 |
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