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

HRID 904411Notes

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

Reactant 3

HCID 260Hydrogen Bromide

HCID 9082Cysteamine Hydrochloride

HCID 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. The base is obtained by basifying with aqueous potassium carbonate, extracting with chloroform, drying the extracts over magnesium sulphate and concentrating. Reacting the amine (5.0 g.) with methyl isothiocyanate (1.94 g.) in ethanol (25 ml.) under reflux for 30 minutes and purifying the product on a column of alumina with benzene as eluant gives N-methyl-N'-[2-(3-methyl-4-isothiazolylmethylthio)ethyl]thiourea. (Found: C, 40.8; H, 5.9; N, 16.1; S, 36.4. C9H15N3S3 requires: C, 41.3; H, 5.8; N, 16.1; S, 36.8).

Sources & evidence

ORD record: ord-64116d85301b43a69d2ab926e9762a2d
Source dataset: uspto-grants-1980_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04230865

Reaction notes

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