1,1-Bis(methylthio)-2-nitroethylene → 1-[(4-Chlorophenyl)methyl]-2-(nitromethylidene)hexahydropyrimidine

HRID 280681Notes

Reaction equation

HRID 280681 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][CH2:8][CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1.[N+:14]([CH:17]=[C:18](SC)SC)([O-:16])=[O:15]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:8][CH2:9][CH2:10][NH:11][C:18]2=[CH:17][N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 2755454N-(4-CHLOROBENZYL)PROPANE-1,3-DIAMINE

Product 1

HCID 678444081-[(4-Chlorophenyl)methyl]-2-(nitromethylidene)hexahydropyrimidineYield 91.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(4-chlorobenzyl)trimethylenediamine (8.45 g) and 1-nitro-2,2-bis(methylthio)ethylene (6.60 g) were heated under reflux in 100 ml of ethanol for 16 hours. The reaction mixture was cooled to room temperature, and the precipitated crystals were collected by filtration and washed with a small amount of ethanol to give 1-(4-chlorobenzyl)-2-(nitromethylene)tetrahydropyrimidine (9.8 g) represented by the following formula. Melting point: 172°-174° C. ##STR10##

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. washwashed with a small amount of ethanol

Sources & evidence

ORD record
ord-84325f58edfd46bab40280c5617ff95f
Source dataset
uspto-grants-1986_05
Patent number
US04590272

Reaction notes

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