4-Bromobenzamide → HCID 178484323, compound

HRID 538987Notes

Reaction equation

HRID 538987 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](/[N:8]=[CH:13]/[N:14]([CH3:16])[CH3:15])=[O:7])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 696834-BromobenzamideHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 178484323HCID 178484323, compoundYield 77.4%

Procedure

A suspension of 4-bromobenzamide (9.50 g, 47.5 mmol) in 1,1-dimethoxy-N,N-dimethylmethanamine (17.2 mL, 47.5 mmol) in a round bottom flask topped with a short path distillation head was placed in a preheated sand bath at 122° C. The reaction mixture was allowed to stir at this temperature for 1.5 hours, during which time the MeOH that was formed was collected from the distillation condenser. Upon cooling solids were formed and collected by vacuum filtration affording (E)-4-bromo-N-((dimethylamino)methylene)benzamide as a pale yellow solid (9.38 g, 77%) which was used directly in the next step without further purification. LCMS (APCI+) m/z 255, 257 [M+H]+.

Workup

  1. distillationtopped with a short path distillation head
  2. customwas placed in a preheated sand bath at 122° C
  3. customwas formed
  4. distillationwas collected from the distillation condenser
  5. temperatureUpon cooling solids
  6. customwere formed
  7. filtrationcollected by vacuum filtration

Sources & evidence

ORD record
ord-da10a2183dad4949b2735694b523e4ba
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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