1,1-Bis(methylthio)-2-nitroethylene → 2-(Nitromethylidene)-1-[(pyridin-4-yl)methyl]hexahydropyrimidine

HRID 1905647Notes

Reaction equation

HRID 1905647 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][NH2:12])=[CH:3][CH:2]=1.[N+:13]([CH:16]=[C:17](SC)SC)([O-:15])=[O:14]>CO>[N:1]1[CH:6]=[CH:5][C:4]([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:3][CH:2]=1

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 13576978N~1~-[(Pyridin-4-yl)methyl]propane-1,3-diamine

Product 1

HCID 702494742-(Nitromethylidene)-1-[(pyridin-4-yl)methyl]hexahydropyrimidineYield 68.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(4-pyridylmethyl)trimethylenediamine (16.5 g), 1-nitro-2,2-bis(methylthio)ethylene (16.5 g) and methanol (100 ml) was refluxed for 2 hours with stirring. The generated gas was collected by an alkali trap. The reaction mixture was cooled to room temperature, and the resulting crystals were filtered to give 1-(4-pyridylmethyl)-2-(nitromethylene)tetrahydropyrimidine (16 g) of the following formulas as pale yellow crystals. Concentrating the filtrate further gave 3 g of this compound. mp. 226°-228° C. ##STR14##

Workup

  1. temperaturewas refluxed for 2 hours
  2. customThe generated gas was collected by an alkali trap
  3. filtrationthe resulting crystals were filtered

Sources & evidence

ORD record
ord-cccfff14a22c462180c6e84496719ad6
Source dataset
uspto-grants-1987_03
Patent number
US04647570

Reaction notes

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