Methanethiol → 1-(1-Methyl-4-pyrazolylmethyl)2-(nitromethylene)tetrahydropyrimidine

HRID 231173Notes

Reaction equation

HRID 231173 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].CS>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

5

Reactant 3

HCID 878MethanethiolHCID 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 was 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. temperaturewas heated
  2. temperatureThe mixture was cooled
  3. filtrationthe precipitated crystals were collected by filtration
  4. washWashing with methanol

Sources & evidence

ORD record
ord-75e64bf492ed437489571fdc056081a7
Source dataset
uspto-grants-1989_07
Patent number
US04845106

Reaction notes

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