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

HRID 1079421Notes

Reaction equation

HRID 1079421 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-a3720dea81a0464b9778c987da46be61
Source dataset
uspto-grants-1996_12
Patent number
US05580889

Reaction notes

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