Dimethylformamide → 2-(4-Chlorophenyl)-3-(dimethylamino)acrylaldehyde

HRID 1980302Notes

Reaction equation

HRID 1980302 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=O)=[CH:9][CH:8]=1.[OH-].[Na+].[CH3:19][N:20]([CH3:23])[CH:21]=O>>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:13](=[CH:19][N:20]([CH3:23])[CH3:21])[CH:14]=[O:16])=[CH:11][CH:12]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 15880(4-Chlorophenyl)acetic acidHCID 24813Phosphorus oxychloride

Product 1

HCID 34489722-(4-Chlorophenyl)-3-(dimethylamino)acrylaldehyde

Procedure

Dimethylformamide (81 grams) was added dropwise to phosphorus oxychloride (138 grams) keeping the temperature at 20°-30° C. by external cooling. The mixture was stirred for 15 minutes at room temperature and then 4-chlorophenylacetic acid (50 grams in 30 ml DMF) was added. After heating to 65°-75° C. for 20 hours, the reaction mixture was cooled, poured onto 1 kilogram of ice and made basic to pH12 with 50% sodium hydroxide, and then heated on a steam bath for 1 hour. The precipitate which formed was filtered, washed with water, dried in vacuo, and then recrystallized from ethyl acetate yielding the desired product, m.p. 117°-120° C.

Workup

  1. customat 20°-30° C.
  2. temperatureAfter heating to 65°-75° C. for 20 hours
  3. temperaturethe reaction mixture was cooled
  4. temperatureheated on a steam bath for 1 hour
  5. customThe precipitate which formed
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried in vacuo
  9. customrecrystallized from ethyl acetate yielding the desired product, m.p. 117°-120° C.

Sources & evidence

ORD record
ord-63bfb76241cd451089e5eebbf5def65a
Source dataset
uspto-grants-1985_04
Patent number
US04508722

Reaction notes

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