GB782971A - Basically substituted carboxylic acid amides and a process for making them - Google Patents

Basically substituted carboxylic acid amides and a process for making them

Info

Publication number
GB782971A
GB782971A GB22794/53A GB2279453A GB782971A GB 782971 A GB782971 A GB 782971A GB 22794/53 A GB22794/53 A GB 22794/53A GB 2279453 A GB2279453 A GB 2279453A GB 782971 A GB782971 A GB 782971A
Authority
GB
United Kingdom
Prior art keywords
methyl
chlorobenzene
amino
reacted
butylamino
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
Application number
GB22794/53A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst AG
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.)
Filing date
Publication date
Application filed by Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB782971A publication Critical patent/GB782971A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)

Abstract

The invention comprises compounds of the formula <FORM:0782971/IV (a)/1> in which R1 represents an alkyl radical having at most 4 carbon atoms, R2 represents an alkylene radical having at most 4 carbon atoms, R3 represents an alkyl or alkenyl radical having at most 5 carbon atoms, and salts of these compounds. Such compounds are obtained by acylating the corresponding substituted aniline with an aliphatic amino-carboxylic acid of the formula HOOC-R2.NHR3 or a functional derivative thereof such as a halide, ester, anhydride, amide or azide, or by acylating the corresponding substituted aniline with a halogen carboxylic acid of the formula HOOC-R2-Hal or a functional derivative thereof such as a halide, ester, anhydride, amide or azide, and then condensing the halogeno-acylamide so obtained with a primary amine of the formula R3NH2. Substituted anilines specified are 1-amino-2-methyl-6-chlorobenzene, 1-amino-2-butyl-6-chlorobenzene, 1-amino-2-methyl-6-bromobenzene, 1 - amino - 2 - propyl - 6 - bromobenzene, 1 - amino - 2 - isopropyl - 6 - chlorobenzene and 1 - amino - 2 - ethyl - 6 - chlorobenzene. As aliphatic aminocarboxylic acids there may be used methyl-, ethyl-, isopropyl- and n-butyl-aminoacetic acids, and ethyl-, butyl- and isopropyl-aminopropionic acids. As halogen-carboxylic acids there are specified chloracetic, a - and b -chloropropionic and a -chlorobutyric acid and the corresponding bromo and iodo compounds (advantageously employed as a halide, amide, ester, anhydride or azide). As primary amines of the formula R3NH2 there may be used methylamine, ethylamine, propylamine and butylamine. The products may be converted to salts with acids such as acetic, lactic, aminosulphonic, phosphoric, hydrochloric or hydrobromic acid. In examples: (1) (a) 1 - amino - 2 - methyl - 6 - chlorobenzene and chloroacetyl chloride are reacted in benzene in the presence of sodium acetate to give 1-(chloracetylamino) - 2 - methyl - 6 - chlorobenzene; (1 (b)) the product of Example 1 (a) is reacted with ethylamine in ethanol to give 1-(ethylamino - acetylamino) - 2 - methyl - 6 - chlorobenzene and its hydrochloride; (2) the product from Example 1 (a) is reacted with n-butylamine to give 1-(butylamino-acetylamino)-2-methyl-6-chlorobenzene (as hydrochloride) from which the free base and the corresponding phosphate are prepared; (3), (4) and (5) the product of Example 1 (a) is reacted with n-propylamine, allylamine and isobutylamine respectively; (6) 1-(a -bromopropionylamino)-2-methyl - 6 - chlorobenzene (from the reaction of 1 - amino - 2 - methyl - 6 - chlorobenzene with a -bromopropionyl chloride) is reacted with butylamine to give 1-(a -butylamino-propionylamino) - 2 - methyl - 6 - chlorobenzene; (7) 1 - (b - chloropropionylamino) - 2 - methyl - 6 - chlorobenzene (from the reaction of 1-amino-2-methyl-6-chlorobenzine and b -chloropropionyl chloride) is reacted with butylamine to form 1-(b - butylamino - propionylamino) - 2 - methyl - 6 - chlorobenzene; (8) phosphorus oxychloride is run into a mixture of chloracetic acid and 1-amino-2-methyl-6-chlorobenzene. The separated product, 1-(chloracetylamino)-2-methyl-6-chlorobenzene, is reacted with butylamine to form 1 - (n - butylamino - acetyl - amino) - 2 - methyl - 6 - chloro - benzene; (9) and (11) the same compound is prepared starting from 1 - amino - 2 - methyl - 6 - chlorobenzene and chloracetyl chloride; (10) 1-(b -chloropropionylamino) - 2 - methyl - 6 - chlorobenzene and n-butylamine are reacted; (12) in a similar process to that of (3), the 1-(chloroacetylamino)-2-methyl-6-chlorobenzene is prepared by the reaction of chloracetyl chloride and 1-amino-2-methyl-6-chlorobenzene in the presence of a fatty acid partial ester of a sorbitol polyglycol ether as emulsifier; (13) 1-(chloracetylamino)-2-methyl - 6 - bromo - benzene (from 1 - amino - 2 - methyl - 6 - bromo - benzene and chloracetyl chloride) and n-butylamine are reacted to give 1 - (butylamino - acetylamino) - 2 - methyl - 6 - bromobenzene; (14) n-butylamino-acetic acid chloride (from butylamino-acetic acid and phosphorus pentachloride in acetyl chloride) is reacted with 1-amino-2-methyl-6-chlorobenzene to give 1-o -butylamino-acetylamino-2-methyl-6-chlorobenzene. Application 22106/98, [Class 81], is referred to.
GB22794/53A 1952-08-18 1953-08-18 Basically substituted carboxylic acid amides and a process for making them Expired GB782971A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE782971X 1952-08-18

Publications (1)

Publication Number Publication Date
GB782971A true GB782971A (en) 1957-09-18

Family

ID=6695754

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22794/53A Expired GB782971A (en) 1952-08-18 1953-08-18 Basically substituted carboxylic acid amides and a process for making them

Country Status (1)

Country Link
GB (1) GB782971A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3412152A (en) * 1965-06-24 1968-11-19 Monsanto Res Corp Nuclearly halogenated dialkenylaminoacetanilides
GB2129424A (en) * 1982-08-27 1984-05-16 Pharmaton Sa Basic acetanilides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3412152A (en) * 1965-06-24 1968-11-19 Monsanto Res Corp Nuclearly halogenated dialkenylaminoacetanilides
GB2129424A (en) * 1982-08-27 1984-05-16 Pharmaton Sa Basic acetanilides

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