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

HRID 1585032Notes

Reaction equation

HRID 1585032 reaction equation
[CH3:1][N:2]([CH3:10])[C:3](SC)=[CH:4][N+:5]([O-:7])=[O:6].C([N:18]([CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)C(NC)=S)C1C=CC=CC=1.[Cl:30]C1N=CC(NC)=CC=1>>[Cl:30][C:27]1[N:26]=[CH:25][C:24]([CH2:23][NH:18][C:3]([N:2]([CH3:10])[CH3:1])=[CH:4][N+:5]([O-:7])=[O:6])=[CH:29][CH:28]=1

Participants

4

Reactant 3

HCID 27267291-Benzyl-3-methyl-1-(pyridin-3-ylmethyl)thioureaHCID 155151186-chloro-N-methylpyridin-3-amineHCID 538966631-Dimethylamino-1-methylthio-2-nitroethylene

Product 1

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

Procedure

The 1-dimethylamino-1-methylthio-2-nitroethylene (1.0 g) prepared in (1) and 1.0 g of 6-chloro-3-pyridyl- methylamine 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. temperaturewere refluxed in 30 ml of EtoH for 2 hours
  2. distillationThe EtOH was then distilled off
  3. customThe crystals obtained
  4. customwere recrystallized from EtOH
  5. customto recover 0.82 g of the title compound as pale yellow crystals

Sources & evidence

ORD record
ord-e033101a5b8d465da52dd9cc2562b4c5
Source dataset
uspto-grants-1999_08
Patent number
US05935981

Reaction notes

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