Dimethylformamide → HCID 57551776, compound

HRID 907287Notes

Reaction equation

HRID 907287 reaction equation
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([CH2:18][CH:19]1[CH2:21][CH2:20]1)[CH:11]=[CH:10]2.CN([CH:25]=[O:26])C>>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([CH2:18][CH:19]1[CH2:20][CH2:21]1)[CH:11]=[C:10]2[CH:25]=[O:26]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 57551774HCID 57551774, compound

Product 1

HCID 57551776HCID 57551776, compound

Procedure

DMF (10 mL) was cooled in an ice bath and phosphorus oxychloride (0.40 mL) was added over 20 seconds. The solution was stirred for 10 minutes at room temperature and then the product of step i) (0.6 g) in DMF (2 mL) was added over 5 minutes. The mixture was heated at 80° C. overnight. The mixture was allowed to cool then poured onto ice/water and stirred for 20 minutes. The aqueous was extracted with ethyl acetate, the organics were combined and evaporated under reduced pressure. The residue was purified (SiO2, eluting with 1:4 ethyl acetate:isohexane) to give the sub-title compound (0.4 g).

Workup

  1. temperatureThe mixture was heated at 80° C. overnight
  2. temperatureto cool
  3. additionthen poured onto ice/water
  4. stirringstirred for 20 minutes
  5. extractionThe aqueous was extracted with ethyl acetate
  6. customevaporated under reduced pressure
  7. customThe residue was purified
  8. wash(SiO2, eluting with 1:4 ethyl acetate:isohexane)

Sources & evidence

ORD record
ord-8100e74b68194298bd126ddc257e8c40
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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