Hydrochloric Acid → L-Penicillamine

HRID 436911

Reaktionsgleichung

Reaktionsgleichung von HRID 436911
C(C1NC(C#N)C(C)(C)S1)(C)C.C#N.Cl.Cl.C(C1[NH:24][CH:23]([C:25]([OH:27])=[O:26])[C:22]([CH3:29])([CH3:28])[S:21]1)(C)C.[Cl-].[NH4+]>>[NH2:24][C@H:23]([C:25]([OH:27])=[O:26])[C:22]([SH:21])([CH3:29])[CH3:28]

Komponenten

6

Edukt 5

HCID 313Hydrochloric AcidHCID 768Hydrogen CyanideHCID 25517Ammonium ChlorideHCID 30147304-Thiazolidinecarboxylic acid, 5,5-dimethyl-2-(1-methylethyl)-, hydrochloride (1:1)HCID 213959112-Isopropyl-5,5-dimethylthiazolidine-4-carbonitrile

Produkt 1

HCID 92863L-Penicillamine

Versuchsvorschrift

In a process for the production of D,L-penicillamine by the reaction of isobutyraldehyde with sulfur and ammonia to form 2-isopropyl-5,5-dimethylthiazoline-3, conversion of the thiazoline with anhydrous hydrogen cyanide into 2-isopropyl-5,5-dimethylthiazolidine-4-carbonitrile, hydrolysis of the nitrile with hydrochloric acid to 2-isopropyl-5,5-dimethylthiazolidine-4-carboxylic acid hydrochloride and ammonium chloride, working up the mixture and separation of the ammonium chloride and hydrolytically breaking down the 2-isopropyl-5,5-dimethylthiazolidine-4-carboxylic acid to form penicillamine the improvement comprising carrying out the hydrolysis of the 2-isopropyl-5,5-dimethylthiazolidine-4-carbonitrile by (1) converting the 2-isopropyl-5,5-dimethylthiazolidine-4-carbonitrile with the hydrochloric acid into 2-isopropyl-5,5-dimethylthiazolidine-4-carbonamide hydrochloride at a temperature of 0° to 80° C and (2) converting the 2-isopropyl-5,5-dimethylthiazolidine-4-carbonamide hydrochloride into 2-isopropyl-5,5-dimethylthiazolidine-4-carboxylic acid hydrochloride at a temperature of 80° to 150° C.

Aufarbeitung

  1. customworking up the mixture and separation of the ammonium chloride

Quellen und Nachweise

ORD-Eintrag
ord-df576b0be07942ea9f1fa2ad6f97d424
Quelldatensatz
uspto-grants-1977_06
Patentnummer
US04028406

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