13206-50-3

Usage

InChI:InChI=1/C9H16N2S/c1-6(2)8-11-7(5-10)9(3,4)12-8/h6-8,11H,1-4H3

Upstream product

• 32899-85-7 2,5-dihydro-5,5-dimethyl-2-(1-methylethyl)-thiazole 
• 74-90-8 hydrogen cyanide 
• 504-79-0 4,5-dihydro-thiazole 

Relevant academic research and scientific papers

Process of making penicillamine

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-Δ3, 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.

Process of preparing penicillamine

Improvements in the process of preparing penicillamine or a homolog thereof by reacting an α-carbon atom branched aldehyde, sulfur and ammonia to form a thiazoline-Δ3, reacting the thiazoline-Δ3 with anhydrous hydrogen cyanide to form a thiazolidine-4-carbonitrile, hydrolyzing the nitrile to form a mixture of the salt of the thiazolidine-4-carboxylic acid and ammonium salts, separating off the ammonium salts and hydrolytically decomposing the thiazolidine-4-carboxylic acid, wherein under the action of a mineral acid the thiazolidine-4-carbonitrile is in the first stage converted at low temperatures into the salt of the thiazolidine-4-carbonamide and then at higher temperatures converted into the salt of the thiazolidine-4-carboxylic acid.

Process of making penicillamine

Penicillamine and its hydrochloride are made by reacting isobutyraldehyde with elemental sulfur or a sulfur-containing compound and with gaseous ammonia so as to form 2-isopropyl-5.5-dimethyl-thiazoline-Δ3, 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.