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

HRID 1834276Notes

Reaction equation

HRID 1834276 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].Cl.NCCS>>[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

4

Reactant 3

HCID 6058CysteamineHCID 9082Cysteamine HydrochlorideHCID 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-e71e018495474df88cd9225b764b648c
Source dataset
uspto-grants-1978_01
Patent number
US04069327

Reaction notes

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