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

HRID 847882

Reaction equation

HRID 847882 reaction equation
[Br:1][C:2]1[C:3]([CH2:7]Br)=[N:4][S:5][CH:6]=1.[NH2:9][CH2:10][CH2:11][SH:12]>>[BrH:1].[Br:1][C:2]1[C:3]([CH2:7][S:12][CH2:11][CH2:10][NH2:9])=[N:4][S:5][CH:6]=1

Participants

3

Reactant 2

HCID 6058CysteamineHCID 205576434-Bromo-3-(bromomethyl)-1,2-thiazole

Product 1

HCID 205500984-Bromo-3-[(2-aminoethyl)thiomethyl]isothiazole hydrobromide

Procedure

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°.

Workup

  1. customFrom the reaction there

Sources & evidence

ORD record
ord-3eae5713489b4a26bc725bfd05dd92ce
Source dataset
uspto-grants-1981_10
Patent number
US04293697

Linked notes

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