Methanethiol → 3-[[2-(Nitromethylene)-1-imidazolidinyl]methyl]pyridine

HRID 376991Notes

Reaction equation

HRID 376991 reaction equation
N1[CH:6]=[C:5]([CH2:7][NH:8][CH2:9][CH2:10][NH2:11])[CH:4]=[N:3][CH:2]=1.[N+:12]([CH:15]=[C:16](SC)SC)([O-:14])=[O:13].[CH3:21]S>C(O)C>[N:3]1[CH:4]=[C:5]([CH2:7][N:8]2[CH2:9][CH2:10][NH:11][C:16]2=[CH:15][N+:12]([O-:14])=[O:13])[CH:6]=[CH:21][CH:2]=1

Participants

5

Reactant 3

HCID 878MethanethiolHCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 13910892N-(5-pyrimidinylmethyl)ethylenediamine

Product 1

HCID 1808863-[[2-(Nitromethylene)-1-imidazolidinyl]methyl]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(5-pyrimidinylmethyl)ethylenediamine (15.2 g), 1-nitro-2,2-bis(methylthio)ethylene (14.9 g) and ethanol (100 g) was refluxed with stirring until the generation of methylmercaptan ceased (for about 3 hours). The reaction mixture was cooled to room temperature, and the resultant crystals were collected by filtration. The crystals were washed with ethanol, and dried to give 1-(5-pyridylmethyl)-2-(nitromethylene)imidazolidine (12.7 g) as pale yellow crystals. This product decomposes at 236° C.

Workup

  1. temperaturewas refluxed
  2. custom(for about 3 hours)
  3. filtrationthe resultant crystals were collected by filtration
  4. washThe crystals were washed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-6b6b5ae9a6d84cb3850efe4cfb837c48
Source dataset
uspto-grants-2000_02
Patent number
US06022967

Reaction notes

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