1-Benzyl-3-methyl-1-(pyridin-3-ylmethyl)thiourea → 1-(6-Chloro-3-pyridylmethyl)amino-1-dimethylamino-2-nitroethylene

HRID 249513Notes

Reaction equation

HRID 249513 reaction equation
[CH3:1][N:2]([CH3:10])[C:3](SC)=[CH:4][N+:5]([O-:7])=[O:6].C(N(CC1C=NC=CC=1)C(NC)=S)C1C=CC=CC=1.[Cl:30][C:31]1[N:36]=[CH:35][C:34]([CH2:37][NH2:38])=[CH:33][CH:32]=1>CCO>[Cl:30][C:31]1[N:36]=[CH:35][C:34]([CH2:37][NH:38][C:3]([N:2]([CH3:10])[CH3:1])=[CH:4][N+:5]([O-:7])=[O:6])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 27267291-Benzyl-3-methyl-1-(pyridin-3-ylmethyl)thioureaHCID 70209275-(Aminomethyl)-2-chloropyridineHCID 538966631-Dimethylamino-1-methylthio-2-nitroethylene

Product 1

HCID 598965901-(6-Chloro-3-pyridylmethyl)amino-1-dimethylamino-2-nitroethylene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The 1-dimethylamino-1-methylthio-2-nitroethylene (1.0 g) prepared in (1) and 1.0 g of 6-chloro-3-pyridylmethylamine were refluxed in 30 ml of EtOH for 2 hours. The EtOH was then distilled off and the residue was subjected to silica gel column chromatography using CHCl3 --MeOH (10:1) as an eluent. The crystals obtained were recrystallized from EtOH to recover 0.82 g of the title compound as pale yellow crystals.

Workup

  1. distillationThe EtOH was then distilled off
  2. customThe crystals obtained
  3. customwere recrystallized from EtOH
  4. customto recover 0.82 g of the title compound as pale yellow crystals

Sources & evidence

ORD record
ord-07402e1b108741ee95e92d28d0d19014
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

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