1,1-Bis(methylthio)-2-nitroethylene → 1-(1-Methyl-4-pyrazolylmethyl)2-(nitromethylene)tetrahydropyrimidine

HRID 1590671Notes

Reaction equation

HRID 1590671 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][NH2:12])[CH:4]=[N:3]1.[N+:13]([CH:16]=[C:17](SC)SC)([O-:15])=[O:14]>C(O)C>[CH3:1][N:2]1[CH:6]=[C:5]([CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][NH:12][C:17]2=[CH:16][N+:13]([O-:15])=[O:14])[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 14207161N-(1-methyl-4-pyrazolylmethyl)trimethylenediamine

Product 1

HCID 702490871-(1-Methyl-4-pyrazolylmethyl)2-(nitromethylene)tetrahydropyrimidineYield 70.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 16.8 g of N-(1-methyl-4-pyrazolylmethyl)-trimethylenediamine, 16.5 g of 1-nitro-2,2-bis(methylthio)ethylene and 200 ml of ethanol wash heated under reflux until the generation of methylmercaptan ceased. The mixture was cooled, and the precipitated crystals were collected by filtration. Washing with methanol gave 16.6 g of the desired 1-(1-methyl-4-pyrazolylmethyl)2-(nitromethylene)tetrahydropyrimidine as pale yellow crystals.

Workup

  1. washwash
  2. temperatureheated
  3. temperatureunder reflux until the generation of methylmercaptan
  4. temperatureThe mixture was cooled
  5. filtrationthe precipitated crystals were collected by filtration
  6. washWashing with methanol

Sources & evidence

ORD record
ord-d9aac6b9b7d54a0287a35f1c226d2446
Source dataset
uspto-grants-1993_04
Patent number
US05204360

Reaction notes

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