1,1-Bis(methylthio)-2-nitroethylene → 1-[3-(2-Guanidinothiazol-4-yl)cyclohexylamino]-1-methylthio-2-nitroethylene

HRID 66573Notes

Reaction equation

HRID 66573 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][S:18][C:19](SC)=[CH:20][N+:21]([O-:23])=[O:22]>C(#N)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]([S:18][CH3:17])=[CH:20][N+:21]([O-:23])=[O:22])[CH2:11]2)[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 1785126122-Guanidino-4-(3-aminocyclohexyl)thiazole

Product 1

HCID 1785038201-[3-(2-Guanidinothiazol-4-yl)cyclohexylamino]-1-methylthio-2-nitroethyleneYield 67.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-guanidino-4-(3-aminocyclohexyl)thiazole (0.5 g.) in boiling acetonitrile (25 ml.) was treated with 1,1-di(methylthio)-2-nitroethylene (0.35 g.) and the mixture heated under reflux for 7 hours. The reaction mixture was evaporated to dryness and the residue crystallised from methanol to give 1-[3-(2-guanidinothiazol-4-yl)cyclohexylamino]-1-methylthio-2-nitroethylene (0.5 g.) as a yellow solid. The n.m.r. spectrum in d6 dimethylsulphoxide included signals at 1.2-2.2(m) 3.3(s), 3.7(m), 6.27(s), 6.65(s) and 6.69(br s)

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 7 hours
  3. customThe reaction mixture was evaporated to dryness
  4. customthe residue crystallised from methanol

Sources & evidence

ORD record
ord-66edcd3e32d0418b99285f44e1ab61a7
Source dataset
uspto-grants-1982_08
Patent number
US04342765

Reaction notes

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