Dimethylformamide dimethyl acetal → HCID 58877886, compound

HRID 1664189Notes

Reaction equation

HRID 1664189 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>CO>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([N:6]=[CH:14][N:15]([CH3:17])[CH3:16])=[O:5]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 27784642-bromo-5-fluorobenzamide

Product 1

HCID 58877886HCID 58877886, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-bromo-5-fluorobenzamide (9.50 g, 43.57 mmol) and N,N-dimethylformamide dimethyl acetal (20 ml) was heated under argon at 120° C. for 1.5 h. The methanol formed during the reaction was collected through a reflux condenser. The reaction mixture was allowed to cool and the excess N,N-dimethylformamide dimethyl acetal was removed under reduced pressure. The residual oil was crystallized from a mixture of ether (75 ml) and hexane (50 ml) to give 8.55 g (72% yield) of the title material as white crystals. 1HNMR 400 MHz (CDCl3) δ (ppm): 3.21 (3H, s, CH3), 3.24 (3H, s, CH3), 7.0 (1H, m, aromatic), 7.58 (1H, dd, J=5.0 Hz and J=8.5 Hz, aromatic), 7.64 (1H, dd, J=3.0 Hz and J=9.1 Hz, aromatic), 8.64 (1H, s, CH).

Workup

  1. customwas collected through a reflux condenser
  2. temperatureto cool
  3. customthe excess N,N-dimethylformamide dimethyl acetal was removed under reduced pressure
  4. customThe residual oil was crystallized from a mixture of ether (75 ml) and hexane (50 ml)

Sources & evidence

ORD record
ord-4ec41c3d30c343dab561c5558cbd8648
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

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