1,1-Dimethoxyethyl(dimethyl)amine → N-[1-(Dimethylamino)ethylidene]-5,6-dichloro-3-pyridinecarboxamide

HRID 368285Notes

Reaction equation

HRID 368285 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([NH2:11])=[O:10])[CH:5]=[N:6][C:7]=1[Cl:8].CO[C:14](OC)([N:16]([CH3:18])[CH3:17])[CH3:15]>>[CH3:17][N:16]([CH3:18])[C:14](=[N:11][C:9]([C:4]1[CH:5]=[N:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)=[O:10])[CH3:15]

Participants

3

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 27821675,6-Dichloropyridine-3-carboxamide

Product 1

HCID 23288262N-[1-(Dimethylamino)ethylidene]-5,6-dichloro-3-pyridinecarboxamideYield 42%

Conditions

Temperature
120 °C

Procedure

A mixture of 5,6-dichloro-3-pyridinecarboxamide (4.0 g, 0.02 mol), dimethylacetamide dimethyl acetal (8 mL) was heated in an oil bath at 120° C. for three hours. The reaction mixture was cooled to room temperature and the solid recrystallised from ethyl acetate:hexane in the presence of activated carbon to give the desired product (2.3 g, 42%) as an orange solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solid recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-8eaf96d195464ac18051453d2c2d61f1
Source dataset
uspto-grants-2000_10
Patent number
US06133294

Reaction notes

Loading…