1-Methylthio-1-methylamino-2-nitroethylene → 1-[3-(4-[2-(2,2,2-Trifluoroethyl)guanidino]pyrimid-2-ylthio)propylamino]-1-methylamino-2-nitroethylene

HRID 364280Notes

Reaction equation

HRID 364280 reaction equation
[F:1][C:2]([F:20])([F:19])[CH2:3][N:4]=[C:5]([NH2:18])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH2:14][CH2:15][CH2:16][NH2:17])[N:8]=1.[CH3:21][NH:22][C:23](SC)=[CH:24][N+:25]([O-:27])=[O:26]>C(#N)C>[F:20][C:2]([F:1])([F:19])[CH2:3][N:4]=[C:5]([NH2:18])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH2:14][CH2:15][CH2:16][NH:17][C:23]([NH:22][CH3:21])=[CH:24][N+:25]([O-:27])=[O:26])[N:8]=1

Participants

4

Reactant 2

HCID 1235491-Methylthio-1-methylamino-2-nitroethyleneHCID 212987114-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(3-aminopropylthio)pyrimidine

Product 1

HCID 704179461-[3-(4-[2-(2,2,2-Trifluoroethyl)guanidino]pyrimid-2-ylthio)propylamino]-1-methylamino-2-nitroethyleneYield 26.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-(3-aminopropylthio)pyrimidine (0.31 g.) in acetonitrile (5 ml.) was treated with 1-methylamino-1-methylthio-2-nitroethylene (0.15 g.) and the mixture heated under reflux for 18 hours. The hot solution was filtered and cooled and the solid which crystallised was collected and recrystallised from ethanol to give 1-[3-(4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimid-2-ylthio)propylamino]-1-methylamino-2-nitroethylene (0.11 g.), m.p. 189°-191°.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 18 hours
  3. filtrationThe hot solution was filtered
  4. temperaturecooled
  5. customthe solid which crystallised
  6. customwas collected
  7. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-cea1f5319a27407c9fe71889c955a246
Source dataset
uspto-grants-1986_08
Patent number
US04604465

Reaction notes

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