Methyl isothiocyanate → HCID 178486101, compound

HRID 66571Notes

Reaction equation

HRID 66571 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH:12]([NH2:16])[CH2:11]2)[N:9]=1)[C:2]([NH2:4])=[NH:3].[CH3:17][N:18]=[C:19]=[S:20].C(Cl)(Cl)Cl.CO.N>C(O)C>[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH:12]([NH:16][C:19]([NH:18][CH3:17])=[S:20])[CH2:11]2)[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

5

Reactant 3

HCID 11167Methyl isothiocyanateHCID 21866414Chloroform methanol ammoniaHCID 1785126122-Guanidino-4-(3-aminocyclohexyl)thiazole

Product 1

HCID 178486101HCID 178486101, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 2-guanidino-4-(3-aminocyclohexyl)thiazole (0.6 g.) in ethanol (20 ml) was added methylisothiocyanate (0.18 g.) and the resulting solution was heated under reflux for two hours. The residue obtained on evaporation of the ethanol was subjected to column chromatography on silica gel (Kiesilgel 60, Merck) using chloroform/methanol/ammonia (s.g. 0.88) 8:2:0.3 v/v/v for development. The product, 2-guanidino-4-[3-(3-methylthioureido)cyclohexyl]thiazole, (0.4 g.) was obtained as a glass. The n.m.r. spectrum, in d6 dimethylsulphoxide, included resonances at 1.2-2.2(m,9H);2.8(d,3H); 4.0(m,1H); 6.2(s,1H); 6.8(br s,4H); and 7.2(br d,2H).

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for two hours

Sources & evidence

ORD record
ord-79818318c5b54ac58f64148de31b4973
Source dataset
uspto-grants-1982_08
Patent number
US04342765

Reaction notes

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