Cysteamine → 4-Bromo-3-[(2-aminoethyl)thiomethyl]isothiazole hydrobromide

The reaction of 4-bromo-3-(bromomethyl)isothiazole (8.5 g.) with cysteamine (from cysteamine hydrochloride (3.76 g.)) was performed under conditions similar to those described in Example 122. From the reaction there was obtained 4-bromo-3-[(2-aminoethyl)thiomethyl]isothiazole hydrobromide, which, following recrystallisation from ethanol-ether and acetonitrile, gave needles (4.05 g.), m.p. 111°-112°. The amine base (2.73 g.) was isolated by basification with sodium hydroxide and extraction with chloroform and then dissolved in ethanol and treated with methyl isothiocyanate (0.78 g.). The solution was heated under reflux for 30 minutes, concentrated and the residue triturated with ether to yield the crystalline thiourea (2.9 g.) m.p. 60°-61°. Recrystallisation from isopropyl acetate gave N-methyl-N'-[2-((4-bromo-3-isothiazolyl)methylthio)ethyl]thiourea (2.3 g.) as needles, m.p. 62°-63°. (Found: C, 29.5; H, 3.8; N, 12.9; Br, 24.6; S, 29.3. C8H12BrN3S3 requires: C, 29.5; H, 3.7; N, 12.9; Br, 24.5; S, 29.5).

1. customFrom the reaction there

ORDレコード

ord-fcac81d12d2147129267fa0de064e3c5

出典データセット

uspto-grants-1979_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04151288