Methyl isothiocyanate → 2-(2-Methylguanidino)-4-[3-(3-methylthioureido)cyclohexyl]thiazole

HRID 66576Notes

Reaction equation

HRID 66576 reaction equation
[CH3:1][N:2]=[C:3]([NH2:17])[NH:4][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.[CH3:18][N:19]=[C:20]=[S:21]>C(O)C>[CH3:1][N:2]=[C:3]([NH2:17])[NH:4][C:5]1[S:6][CH:7]=[C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH:12]([NH:16][C:20]([NH:19][CH3:18])=[S:21])[CH2:11]2)[N:9]=1

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 205303852-(2-Methylguanidino)-4-(3-aminocyclohexyl)thiazole

Product 1

HCID 205303842-(2-Methylguanidino)-4-[3-(3-methylthioureido)cyclohexyl]thiazoleYield 90.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(2-methylguanidino)-4-(3-aminocyclohexyl)thiazole (0.3 g.) in ethanol (50 ml.) was added methylisothiocyanate (0.1 g.) and the solution heated under reflux for 2 hours. Evaporation of the reaction mixture and crystallisation of the residue from methanol/ethyl acetate gave 2-(2-methylguanidino)-4-[3-(3-methylthioureido)cyclohexyl]thiazole (0.35 g.), m.p. 214°-215° (decomp.).

Workup

  1. temperaturethe solution heated
  2. temperatureunder reflux for 2 hours
  3. customEvaporation of the reaction mixture and crystallisation of the residue from methanol/ethyl acetate

Sources & evidence

ORD record
ord-01cec03b83f148ffadff8b066265cf51
Source dataset
uspto-grants-1982_08
Patent number
US04342765

Reaction notes

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