Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1974-08-01
1976-03-16
Sneed, Helen M. S.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
C07C 8900, C07C 9104
Patent
active
039446174
ABSTRACT:
DL-2-Amino-1-butanol, as the free base or a salt, for resolution to d-2-amino-1-butanol, 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 dl-2-amino-1-butanol hydrochloride. This 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. A minimum of by-products which are conveniently split out permits the economical synthesis of a pharmaceutical grade product.
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Chemical Abstracts, V. 79, 65780e (1973).
J.A.C.S. V. 83, pp. 2212-2213 (1961).
J.A.C.S. V. 76, pp. 2801-2803 (1954).
American Cyanamid Company
Sneed Helen M. S.
Walker Samuel Branch
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