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

HRID 847986Notes

Reaction equation

HRID 847986 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 1 gives 3-methyl-4-[-(2-aminoethyl)thiomethyl]isothiazole hydrobromide. Treatment of this intermediate with aqueous potassium carbonate, extracting with chloroform, drying the chloroform extract over magnesium sulphate and concentrating gives the free base, 5.0 g. of which is then reacted with methyl isothiocyanate (1.94 g.) in ethanol (25 ml.) under reflux for 30 minutes. The product is purified on a column of alumina and elution with benzene gives N-methyl-N'-[2-((3-methyl-4-isothiazolyl)methylthio)ethyl]thiourea. Reaction of this product by the procedure of Example 121 gives N-cyano-N'-methyl-N"-[2-((3-methyl-4-isothiazolyl)methylthio)ethyl]guanidine.

Sources & evidence

ORD record
ord-4f284db08ca9469a81ced9216aa98042
Source dataset
uspto-grants-1981_10
Patent number
US04293699

Reaction notes

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