Methyl isothiocyanate → 2-[2-(2,2,2-Trifluoroethyl)guanidino]-4-[2-(3-methylthioureido)ethylthiomethyl]thiazole

HRID 34758Notes

Reaction equation

HRID 34758 reaction equation
[CH3:1][N:2]=[C:3]=[S:4].[F:5][C:6]([F:23])([F:22])[CH2:7][N:8]=[C:9]([NH2:21])[NH:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][S:17][CH2:18][CH2:19][NH2:20])[N:15]=1>CO>[F:23][C:6]([F:5])([F:22])[CH2:7][N:8]=[C:9]([NH2:21])[NH:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][S:17][CH2:18][CH2:19][NH:20][C:3]([NH:2][CH3:1])=[S:4])[N:15]=1

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 141820862-[2-(2,2,2-Trifluoroethyl)guanidino]-4-[(2-aminoethyl)thiomethyl]thiazole

Product 1

HCID 212987002-[2-(2,2,2-Trifluoroethyl)guanidino]-4-[2-(3-methylthioureido)ethylthiomethyl]thiazoleYield 22.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl isothiocyanate (80 mg.) was added to 2-[2-(2,2,2-trifluoroethyl)guanidino]-4-[(2-aminoethyl)thiomethyl]thiazole (320 mg.) dissolved in methanol (5 ml.) and the solution kept at room temperature for 18 hours and then evaporated to dryness. The residual gum was purified by preparative thin layer chromatography using ethyl acetate/methanol/ammonia 6:1:0.5 v/v/v as developing solvent to give 2-[2-(2,2,2-trifluoroethyl)guanidino]-4-[2-(3-methylthioureido)ethylthiomethyl]thiazole (90 mg.), characterised as the hydrogen maleate, m.p. 137°139° (decomp.) (after crystallisation from acetonitrile.).

Workup

  1. customevaporated to dryness
  2. customThe residual gum was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-80951e2132c4433280a2b0d00093c4e9
Source dataset
uspto-grants-1988_08
Patent number
US04762932

Reaction notes

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