5-Amino-2-chloropyridine → 1-(6-Chloro-3-pyridyl)amino-1-dimethylamino-2-nitroethylene

HRID 1954993Notes

Reaction equation

[CH3:1][N:2]([CH3:10])[C:3](SC)=[CH:4][N+:5]([O-:7])=[O:6].[NH2:11][C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[N:16][CH:17]=1>CCO.C(Cl)(Cl)Cl>[Cl:18][C:15]1[N:16]=[CH:17][C:12]([NH:11][C:3]([N:2]([CH3:10])[CH3:1])=[CH:4][N+:5]([O-:7])=[O:6])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 115 °C

Procedure

A mixture of 1.5 g (0.0093 mole) of 1-dimethylamino-1-methylthio-2-nitroethylene and 1.1 g of 5-amino-2-chloropyridine was heated at 110-120° C. with stirring for 1 hour. After cooling, the reaction mixture was subjected to silica gel column chromatography using EtOH-CHCl3 (1:40) as the eluent to recover 0.38 g of the title compound as pale brown crystals. The NMR spectrum of this product showed that it was a 1:1 mixture of the title compound and N2 -(6-chloro-3-pyridyl)-N'-dimethyl-2-nitroacetamidine.

Workup

temperatureAfter cooling
customto recover 0.38 g of the title compound as pale brown crystals
additiona 1:1 mixture of the title compound and N2 -(6-chloro-3-pyridyl)-N'-dimethyl-2-nitroacetamidine

Sources & evidence

ORD record: ord-bfa02c5e366b4989889771b93d045579
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06124297

Reaction notes

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