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

HRID 597414

Reaction equation

HRID 597414 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 47. 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.

Workup

  1. customFrom the reaction there

Sources & evidence

ORD record
ord-289e6d9471154ff5aea0d19418cb65de
Source dataset
uspto-grants-1977_03
Patent number
US04013769

Linked notes

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