Dimethylformamide → HCID 13393786, compound

HRID 2107719Notes

Reaction equation

HRID 2107719 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:8][C:7]2=O)([OH:3])=[O:2].P(Cl)(Cl)([Cl:23])=O.CN(C)[CH:28]=[O:29]>>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]([CH:28]=[O:29])=[C:7]2[Cl:23])([OH:3])=[O:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 52705532H-1-Benzopyran-6-carboxylic acid, 3,4-dihydro-4-oxo-2-phenyl-

Product 1

HCID 13393786HCID 13393786, compound

Procedure

As in example 1, but using 6 g 6-carboxy-flavanone, 60 ml dimethylformamide and 15 ml phosphorous oxychloride. Reaction time is three hours at 50° C. After hydrolysis a precipitate formed which is filtered, washed with water and dried over phosphorous pentoxyde. The residual solid is dissolved in a 10% sodium bicarbonate aqueous solution, which is then washed with methylene chloride. The aqueous phase is acidified with a 10% hydrochloric acid solution and the precipitate which formed is filtered, washed and dried. The residual solid is recrystallised in a mixture of hexane and ethyl acetate and pure 6-carboxy-4-chloro-3-formyl-flav-3-ene is obtained; m.p. 262°-267° C.

Workup

  1. customReaction time
  2. customAfter hydrolysis a precipitate
  3. customformed which
  4. filtrationis filtered
  5. washwashed with water
  6. customdried over phosphorous pentoxyde
  7. dissolutionThe residual solid is dissolved in a 10% sodium bicarbonate aqueous solution, which
  8. washis then washed with methylene chloride
  9. customthe precipitate which formed
  10. filtrationis filtered
  11. washwashed
  12. customdried
  13. customThe residual solid is recrystallised in a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-251c8db8d90b48c6b45e0762e1ba07da
Source dataset
uspto-grants-1990_06
Patent number
US04935441

Reaction notes

Loading…