Dimethylformamide dimethyl acetal → HCID 76716666, compound

HRID 253968Notes

Reaction equation

HRID 253968 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9](=[O:19])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=2[Cl:18])[C:5]([Cl:8])=[N:6][CH:7]=1.[CH3:20][N:21]([CH:23](OC)OC)[CH3:22]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:9](=[O:19])[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=2[Cl:18])=[CH:20][N:21]([CH3:23])[CH3:22])[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 58179505HCID 58179505, compound

Product 1

HCID 76716666HCID 76716666, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(5-bromo-2-chloropyridin-3-yl)-2-(2,3-dichlorophenyl)ethanone in dry THF was slowly treated with DMF-DMA under N2 atmosphere for 45 min and stirred at RT until completion of the reaction. The reaction mixture was concentrated under reduced pressure to obtain 1-(5-bromo-2-chloropyridin-3-yl)-2-(2,3-dichlorophenyl)-3-(dimethylamino)prop-2-en-1-one as semi solid. Washing the crude product with n-pentane and pet-ether resulted in a free flowing light brown solid (1.0 g, 58.8%) which was used as is in the next reaction without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-714ddf8e15b044f8aceb0d31db64bf27
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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