Dimethylformamide dimethyl acetal → 4-Bromo-N-[(dimethylamino)methylene]-2-fluoro-5-methylbenzamide

HRID 717149Notes

Reaction equation

HRID 717149 reaction equation
[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([F:12])[CH:3]=1.CO[CH:15](OC)[N:16]([CH3:18])[CH3:17]>>[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]([C:6]([N:8]=[CH:15][N:16]([CH3:18])[CH3:17])=[O:7])=[C:4]([F:12])[CH:3]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 66606809HCID 66606809, compound

Product 1

HCID 666078964-Bromo-N-[(dimethylamino)methylene]-2-fluoro-5-methylbenzamideYield 95%

Procedure

A solution of 4-bromo-2-fluoro-5-methylbenzamide (20 g, 86 mmol) in N,N-dimethyl-formamide dimethylacetal (200 mL) was stirred at 100° C. under nitrogen for 3 h. The resulting mixture was concentrated and dried to give the desired product (24.6 g, 95% yield) as a yellow oil, which was used in the next step without further purification. MS (ESI) m/z 287.0 [M+1]+.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. customdried

Sources & evidence

ORD record
ord-aa582b805c5f47809b14cb41a4550610
Source dataset
uspto-grants-2015_11
Patent number
US09193692B2

Reaction notes

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