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

HRID 34762Notes

Reaction equation

HRID 34762 reaction equation
[F:1][C:2]([F:19])([F:18])[CH2:3][N:4]=[C:5]([NH2:17])[NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])[N:11]=1.[CH3:20][N:21]=[C:22]=[S:23].C(Cl)(Cl)Cl.CO.N>CO>[F:19][C:2]([F:1])([F:18])[CH2:3][N:4]=[C:5]([NH2:17])[NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:22]([NH:21][CH3:20])=[S:23])[N:11]=1

Participants

5

Reactant 3

HCID 11167Methyl isothiocyanateHCID 212987102-[2-(2,2,2-Trifluoroethyl)-guanidino]-4-(4-aminobutyl)thiazoleHCID 21866414Chloroform methanol ammonia

Product 1

HCID 212988512-[2-(2,2,2-Trifluoroethyl)guanidino]-4-[4-(3-methylthioureido)butyl]thiazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-[2-(2,2,2-trifluoroethyl)guanidino]-4-(4-aminobutyl)thiazole (0.3 g.) and methyl isothiocyanate (0.18 g.) in methanol (6 ml.) was allowed to stand at room temperature for 3 hours. The residue obtained on evaporation of the solvent was subjected to preparative thin layer chromatography using chloroform/methanol/ammonia 90:10:0.5 v/v/v for development. The appropriate zone of the chromatogram was isolated and extracted with hot ethanol/chloroform 50:50 v/v (100 ml.). Evaporation of the solvent gave 2-[2-(2,2,2-trifluoroethyl)guanidino]-4-[4-(3-methylthioureido)butyl]thiazole as a straw-coloured gum. The n.m.r. spectrum d6 dimethylsulphoxide using tetramethylsilane as internal standard included the following resonances (δ): 2.75 (3H, doublet), 4.04 (2H, multiplet) and 6.34 (1H, singlet). On addition of D2O the multiplet at δ4.04 collapsed to a quartet.

Workup

  1. customThe residue obtained on evaporation of the solvent
  2. customThe appropriate zone of the chromatogram was isolated
  3. extractionextracted with hot ethanol/chloroform 50:50 v/v (100 ml.)
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-c1e017087cab42ada2160b35d74ad61f
Source dataset
uspto-grants-1988_08
Patent number
US04762932

Reaction notes

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