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

HRID 1252126Notes

Reaction equation

HRID 1252126 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-29f6f24ea07c4d25b05362aac85e2ded
Source dataset
uspto-grants-1988_05
Patent number
US04742060

Reaction notes

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