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

HRID 1902282Notes

Reaction equation

HRID 1902282 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-b5264bd8091c45c19973048c7fbd81c8
Source dataset
uspto-grants-1982_12
Patent number
US04362728

Reaction notes

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