Process of making penicillamine
AssigneeDeutsche Gold- und Silber-Scheideanstalt vormals Roessler
InventorsFriedrich Asinger, Heribert Offermanns, Miklos Ghyczy
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Abstract
Penicillamine and its hydrochloride are made by reacting i-butyraldehyde with elemental sulfur or a sulfur-containing compound and with gaseous ammonia so as to form 2-isopropyl-5.5-dimethyl-thiazoline-.DELTA..sup.3, then reacting the latter compound with substantially anhydrous hydrogen cyanide so as to form the corresponding thiazolidine 4-carbonitrile, thereupon treating the latter compound with an excess of concentrated hydrochloric acid at an elevated temperature and separating the components of the mixture formed and recovering the penicillamine hydrochloride which may then be converted to the free D,L-penicillamine.
Claims10
In a process for the production of D,L-penicillamine or its hydrochloride by reacting 2-isopropyl-5,5-dimethylthiazoline-3 with hydrogen cyanide to form 2-isopropyl-5,5-dimethylthiazoline-4-carbonitrile, hydrolysis of the nitrile with hydrochloric acid to form 2-isopropyl-5,5-dimethylthiazolidine-4-carboxylic acid hydrocloride and converting said 2-isopropyl-5,5-dimethylthiazolidine-4-carboxylic acid hydrochloride to penicillamine hydrochloride the improvement consisting of:
- a. reacting 2-isopropyl-5,5-dimethylthiazoline-3 with substantially anhydrous hydrogen cyanide to form said thiazolidine carbonitrile,
- b. heating said thiazolidine carbonitrile with excess concentrated hydrochloric acid at a temperature between about 70.degree. C. and 110.degree. C. to form said thiazolidine carboxylic acid hydrochloride, and,
- c. converting said thiazolidine carboxylic acid hydrochloride to penicillamine hydrochloride by subjecting it to a steam distillation.
Dependencies are inferred from the claim text.