Methyl isothiocyanate → N-methyl-N'-[2-(5-thiazolylmethylthio)ethyl]thiourea

HRID 903248

Reaction equation

HRID 903248 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[S:10][CH:9]=[N:8][CH:7]=1.[CH3:11][N:12]=[C:13]=[S:14]>C(O)C>[CH3:11][NH:12][C:13]([NH:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[S:10][CH:9]=[N:8][CH:7]=1)=[S:14]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 129234072-{[(1,3-Thiazol-5-yl)methyl]sulfanyl}ethan-1-amine

Product 1

HCID 12923382N-methyl-N'-[2-(5-thiazolylmethylthio)ethyl]thiourea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The reaction of 5-[(2-aminoethyl)thiomethyl]thiazole (2.24 g.) with methyl isothiocyanate (0.94 g.) in ethanol (10 ml.) gave a thiourea which was purified by chromatography on a column of silica gel with ethyl acetate as eluant. Recrystallisation from isopropyl acetate-methyl ethyl ketone-ether gave N-methyl-N'-]2-(5-thiazolylmethylthio)ethyl]thiourea (2.1 g.), m.p. 86°-88°. (Found: C, 38.6; H, 5.4; N, 16.9; S, 38.6. C8H13N3S3 requires: C, 38.8; H, 5.3; N, 17.0; S, 38.9).

Sources & evidence

ORD record
ord-2f594354d09f4634b04f85d224381c3d
Source dataset
uspto-grants-1980_10
Patent number
US04226874

Linked notes

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