GB648886A - Improvements in or relating to the preparation of amides and/or amino acids - Google Patents
Improvements in or relating to the preparation of amides and/or amino acidsInfo
- Publication number
- GB648886A GB648886A GB7560/47A GB756047A GB648886A GB 648886 A GB648886 A GB 648886A GB 7560/47 A GB7560/47 A GB 7560/47A GB 756047 A GB756047 A GB 756047A GB 648886 A GB648886 A GB 648886A
- Authority
- GB
- United Kingdom
- Prior art keywords
- propiolactone
- phenyl
- amines
- primary
- nitrogen
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C241/04—Preparation of hydrazides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
N-substituted amides of b -hydroxycarboxylic acids and N-substituted amino-acids are prepared by reacting b -lactones with (a) aliphatic or cycloaliphatic unsubstituted primary or secondary amines or aliphatic or cycloaliphatic substituted primary or secondary amines in which no substituent is a neutralized acidic group, or (b) unsaturated cyclic primary amines containing only carbon, hydrogen, and nitrogen, or (c) hydrazines p or amidines. The amides may lose water to give the corresponding amides of a ,b -unsaturated carboxylic acids. The b -lactones may be obtained from reaction of ketenes with aldehydes or ketones as in Specification 649,028. The amines used include alkyl, alkenyl, and alkynyl monamines, alkylene diamines and polyamines, which are exemplified, aryl-substituted aliphatic primary amines, e.g. benzylamine, benzohydrylamine, phenyl ethylamine, and p-xylylene diamine, alicyclic primary amines such as cyclohexylamine, and cyclohexylene diamines, aromatic primary monoamines, and diamines or polyamines wherein at least one amine group is primary, heterocyclic amines, e.g. pyridyl, and quinolyl amines, secondary aliphatic and cyclic monoamines, including dicyclohexylamine, ethyleneimine, piperidine and pipecolines, and polyamines such as piperazine, other primary and secondary amines containing other nitrogen atoms in addition to hydrogen-bearing nitrogen, e.g. b -(diethylamino)-ethylamine, and b -cyanoethylamine, or containing oxygen in oxy and/or oxo groups, e.g. furfurylamine, morpholine, b - ethoxy - ethylamine, hydroxy - substituted amines, acetonylamine, amino-acids, and their esters and amides, and compounds where oxygen is in oxo groups linked to nitrogen other than amino nitrogen, e.g. b -nitro-ethylamine, or containing other elements such as sulphur, chlorine or bromine instead of or in addition to oxygen, e.g. chlorethylamine, 2,3-dichlorpropylamine, aminomethyl ethyl sulphide, b ,b 1-diamino ethyl sulphide, g -mercapto-propylamine, cysteine, cystine, and taurine. Hydrazines include phenyl, ethyl, and benzyl hydrazines, and amidines include acetamidine, guanidine, guanylhydrazine, and dicyandiamide. The invention is illustrated by reactions of b -propiolactone with methylamine, dimethylamine, diethanolamine, aniline, and phenylhydrazine. Other b -lactones used include b -isobutyrolactone, n - butyrolactone, valerolactone, isovalerolactone, n-caprolactone, a -ethyl, isopropyl or butyl b -propiolactone, b - methyl - b - valerolactone, b - cyclohexyl, phenyl or benzyl b -propiolactone, and other compounds having the b -lactone structure and groups containing elements such as oxygen, nitrogen, sulphur, and halogen attached to the a - and b -carbons, e.g. b ,b -dimethyl-b -propiolactone - a - carboxylic acid, b - (o - nitro - m - chlor-phenyl)-b -propiolactone, and a -bromob ,b -dimethyl-b -propiolactone-a -carboxylic acid. Solvents and diluents may be used, especially with solid reactants. Temperature is generally below 100, from - 10 DEG to 50 DEG C. being preferred. The products are used in preparing monomers for synthetic resin and rubber, and for production of artificial fibres, plasticizers, and pharmaceuticals. In examples: (1) b -propiolactone is added to aniline at 10-30 DEG C., giving N-phenyl hydracrylamide, which on distillation yields N-phenyl acrylamide, and b -N-phenyl-amino-propionic acid. The N-phenyl hydracrylamide is cyclized, e.g. with aluminium chloride, to give hydrocarbostyril; (2) b -propiolactone is added to aqueous aniline hydrochloride at 20 DEG C. and the product distilled; (3) p-toluidine similarly gives N-(p-toluyl)-hydracrylamide and acrylamide; (4) o- or p-phenylenediamine is converted to its hydracrylamide; (5) methylamine reacts similarly at - 10 DEG C. yielding N-methylhydracrylamide and acrylamide; (6) phenylhydrazine yields hydracrylphenylhydrazide; (7) and (8) dimethylamine and diethylamine give similar products as does ethyleneimine; (9) morpholine yields N-carboxyethyl morpholine; (10) and (11) diethanolamine and ethanolamine give NN-di-2-hydroxyethyl and N-2-hydroxyethyl-b -amino-propionic acid respectively; (12) glycine yields N-carboxymethyl hydracrylamide.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US648886XA | 1946-03-21 | 1946-03-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB648886A true GB648886A (en) | 1951-01-17 |
Family
ID=22058883
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7560/47A Expired GB648886A (en) | 1946-03-21 | 1947-03-19 | Improvements in or relating to the preparation of amides and/or amino acids |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB648886A (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2850486A (en) * | 1953-06-26 | 1958-09-02 | Koppers Co Inc | Polymerization products of the dialkyl aryl amides of cyano-acrylic acids |
US2955137A (en) * | 1958-05-08 | 1960-10-04 | Gen Aniline & Film Corp | Heat treated reaction products of n-alkylaminopropyl-gamma-hydroxybutyramides |
US3025323A (en) * | 1957-01-18 | 1962-03-13 | Union Carbide Corp | Amide diols and their esters |
US7538247B2 (en) | 2004-04-02 | 2009-05-26 | Ciba Specialty Chemicals Corporation | Preparation of acrylic acid derivatives from α- or β-hydroxy carboxylic acids |
US20110083957A1 (en) * | 2008-04-04 | 2011-04-14 | Clariant Finance (Bvi) Limited | Continuous Method For Producing Amides Of Aliphatic Hydroxycarboxylic Acids |
CN118439966A (en) * | 2024-07-05 | 2024-08-06 | 南昌大学 | Synthesis method of p-nitroaniline compound |
-
1947
- 1947-03-19 GB GB7560/47A patent/GB648886A/en not_active Expired
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2850486A (en) * | 1953-06-26 | 1958-09-02 | Koppers Co Inc | Polymerization products of the dialkyl aryl amides of cyano-acrylic acids |
US3025323A (en) * | 1957-01-18 | 1962-03-13 | Union Carbide Corp | Amide diols and their esters |
US2955137A (en) * | 1958-05-08 | 1960-10-04 | Gen Aniline & Film Corp | Heat treated reaction products of n-alkylaminopropyl-gamma-hydroxybutyramides |
US7538247B2 (en) | 2004-04-02 | 2009-05-26 | Ciba Specialty Chemicals Corporation | Preparation of acrylic acid derivatives from α- or β-hydroxy carboxylic acids |
US20110083957A1 (en) * | 2008-04-04 | 2011-04-14 | Clariant Finance (Bvi) Limited | Continuous Method For Producing Amides Of Aliphatic Hydroxycarboxylic Acids |
CN118439966A (en) * | 2024-07-05 | 2024-08-06 | 南昌大学 | Synthesis method of p-nitroaniline compound |
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