Dimethylformamide dimethyl acetal → HCID 178484324, compound

HRID 538993Notes

Reaction equation

HRID 538993 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([F:11])[CH:3]=1.CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](/[N:8]=[CH:14]/[N:15]([CH3:17])[CH3:16])=[O:7])=[C:4]([F:11])[CH:3]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 27733314-Bromo-2-fluorobenzamide

Product 1

HCID 178484324HCID 178484324, compoundYield 96%

Conditions

Temperature
100 °C

Procedure

A suspension of 4-bromo-2-fluorobenzamide (0.929 g, 4.26 mmol) in 1,1-dimethoxy-N,N-dimethylmethanamine (1.66 mL, 11.7 mmol) in a round bottom flask topped with a short path distillation head was heated to 100-100° C. The resulting solution was allowed to stir at this temperature for 3.5 hours, during which time the MeOH that was formed was collected from the distillation condenser. Heptane (5 mL) was added dropwise and the resulting suspension was cooled to 0-5° C. The solids were collected by vacuum filtration, rinsed with excess heptane, and dried to afford (E)-4-bromo-N-((dimethylamino)methylene)-2-fluorobenzamide (1.111 g, 96%) as an off-white solid which was carried on without further purification.

Workup

  1. distillationtopped with a short path distillation head
  2. customwas formed
  3. distillationwas collected from the distillation condenser
  4. additionHeptane (5 mL) was added dropwise
  5. temperaturethe resulting suspension was cooled to 0-5° C
  6. filtrationThe solids were collected by vacuum filtration
  7. washrinsed with excess heptane
  8. customdried

Sources & evidence

ORD record
ord-e7785fe88bcf49729865d73fc3f9046e
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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