Synthesis of N-[1-(chloromethyl)propyl]acetamide

Details Synthesis of N-[1-(chloromethyl)propyl]acetamide Synthesis of N-[1-(chloromethyl)propyl]acetamide

1974-08-01

1976-03-16

Davis, C.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260561R, C07C10334

Patent

active

039446085

ABSTRACT:
N-[1-(Chloromethyl)propyl]acetamide, for the synthesis of ethambutol hydrochloride, d,d'-2,2'-(ethylenediimino)-di-1-butanol dihydrochloride, is produced in high purity and good yields by the reaction of butene-1, a nitrile, preferably an excess of acetonitrile, and chlorine to form N-[1-(chloromethyl)propyl]acetimidoyl chloride which is hydrolyzed to N-[1-(chloromethyl)propyl]acetamide. This may be hydrolyzed further to dl-2-amino-1-butanol, which can be isolated as the hydrochloride, or free base, or a mixture, resolved with L(+)-tartaric acid and the d-2-amino-1-butanol reacted with ethylene dichloride and then hydrochloric acid to form ethambutol hydrochloride.

REFERENCES:
patent: 2569549 (1951-10-01), Barrick
patent: 3855300 (1974-12-01), Takahashi et al.

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