Acetonitrile → HCID 86738515, compound

HRID 66577Notes

Reaction equation

HRID 66577 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.CS[C:20](SC)=[CH:21][N+:22]([O-:24])=[O:23].[C:27](#[N:29])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:29][CH3:27])=[CH:21][N+:22]([O-:24])=[O:23])[CH2:11]2)[N:9]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 205303852-(2-Methylguanidino)-4-(3-aminocyclohexyl)thiazole

Product 1

HCID 86738515HCID 86738515, compound

Procedure

To a solution of 2-(2-methylguanidino)-4-(3-aminocyclohexyl)thiazole (0.2 g.) in acetonitrile (20 ml.) was added 1,1-di(methylthio)-2-nitroethylene (0.125 g.) and the mixture heated under reflux for 7 hours. The reaction mixture was evaporated to dryness and the residue of 1-[3-[2-(2-methylguanidino)thiazol-4-yl]cyclohexylamino]-1-methylthio-2-nitroethylene, dissolved in ethanol (20 ml.), was treated with 20 ml. of a solution of methylamine in ethanol (33% w/v). The reaction mixture was allowed to stand overnight. Evaporation of the solvent and recrystallisation of the residue from methanol gave 1-[3-[2-(2-methylguanidino)thiazol-4-yl]cyclohexylamino]-1-methylamino-2-nitroethylene, m.p. 164°-174° (decomp.).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 7 hours
  3. customThe reaction mixture was evaporated to dryness
  4. dissolutionthe residue of 1-[3-[2-(2-methylguanidino)thiazol-4-yl]cyclohexylamino]-1-methylthio-2-nitroethylene, dissolved in ethanol (20 ml.)
  5. additionwas treated with 20 ml
  6. customEvaporation of the solvent and recrystallisation of the residue from methanol

Sources & evidence

ORD record
ord-b0b8410c79ab4d6080059c5383b1c38b
Source dataset
uspto-grants-1982_08
Patent number
US04342765

Reaction notes

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