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

HRID 364258Notes

Reaction equation

HRID 364258 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-99746b181cc74dc4a27f9125bdee2833
Source dataset
uspto-grants-1986_08
Patent number
US04604465

Reaction notes

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