Hydrogen Bromide → 3-Methyl-4-[(2-aminoethyl)thiomethyl]isothiazole hydrobromide

HRID 27115Notes

Reaction equation

HRID 27115 reaction equation
O[CH2:2][C:3]1[C:4]([CH3:8])=[N:5][S:6][CH:7]=1.Cl.[NH2:10][CH2:11][CH2:12][SH:13].[BrH:14]>>[BrH:14].[CH3:8][C:4]1[C:3]([CH2:2][S:13][CH2:12][CH2:11][NH2:10])=[CH:7][S:6][N:5]=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 9082Cysteamine HydrochlorideHCID 20550175(3-Methyl-1,2-thiazol-4-YL)methanol

Product 1

HCID 205501323-Methyl-4-[(2-aminoethyl)thiomethyl]isothiazole hydrobromide

Procedure

Reacting 4-hydroxymethyl-3-methylisothiazole (3.0 g) with cysteamine hydrochloride (2.8 g) in 48% aqueous hydrobromic acid (50 ml) by the procedure of Example 42(ii) gives 3-methyl-4-[(2-aminoethyl)thiomethyl]isothiazole hydrobromide. The base is obtained by basifying with aqueous potassium carbonate, extracting with chloroform, drying the extracts over magnesium sulphate and concentrating. Using the amine (5.0 g) as the starting material in the procedure of Example 72(ii) yields the title compound.

Sources & evidence

ORD record
ord-8e2769847b78454e8444833ee07cc239
Source dataset
uspto-grants-1980_09
Patent number
US04220652

Reaction notes

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