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

HRID 1902260Notes

Reaction equation

HRID 1902260 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-2642b19981c44c1883651c119f0c80bd
Source dataset
uspto-grants-1982_12
Patent number
US04362728

Reaction notes

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