1,1-Bis(methylthio)-2-nitroethylene → 2-(Nitromethylene)imidazolidine

HRID 1905648Notes

Reaction equation

HRID 1905648 reaction equation
N1C=CC=C(C[NH:8][CH2:9][CH2:10][NH2:11])C=1.[N+:12]([CH:15]=[C:16](SC)SC)([O-:14])=[O:13]>C1C=CC=CC=1>[N+:12]([CH:15]=[C:16]1[NH:11][CH2:10][CH2:9][NH:8]1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 106306911,2-Ethanediamine, N-(3-pyridinylmethyl)-

Product 1

HCID 30147632-(Nitromethylene)imidazolidineYield 131.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of N-(3-pyridylmethyl)ethylenediamine (15.1 g), 1-nitro-2,2-bis(methylthio)ethylene (18.2 g) and benzene (150 ml) was refluxed for 4 hours with stirring. The generated gas was collected by an alkali trap. The reaction mixture was cooled to room temperature, and filtered to collect crystals. Recrystallization from methanol gave 1-(3-pyridylmethyl)-2-(nitromethylene imidazolidine (17 g) of the following formula as pale yellow crystals. mp. 169°-171° C. ##STR15##

Workup

  1. temperaturewas refluxed for 4 hours
  2. customThe generated gas was collected by an alkali trap
  3. filtrationfiltered
  4. customto collect crystals
  5. customRecrystallization from methanol

Sources & evidence

ORD record
ord-7d75490e76fc4b4f952528a8ad0a1bb7
Source dataset
uspto-grants-1987_03
Patent number
US04647570

Reaction notes

Loading…