4-Hydroxybenzaldehyde → HCID 22168763, compound

HRID 1611418Notes

Reaction equation

HRID 1611418 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.[CH3:16][C:17]1[N:21]([CH:22](S(OC)(=O)=O)[CH3:23])[C:20]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:19][CH:18]=1>CN(C)C=O.O>[CH3:16][C:17]1[N:21]([CH2:22][CH2:23][O:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=2)[C:20]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 22168755HCID 22168755, compound

Product 1

HCID 22168763HCID 22168763, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of potassium carbonate (16.43 g) in dimethyl formamide (50 mL), 4-hydroxy benzaldehyde (4.37 g) was added and warmed to 90° C. to 95° C. To the solution, methyl 1-[5-methyl-2-phenyl-1H-pyrrol-1yl]ethane sulfonate (10 g) (compound no. 41) dissolved in dimethyl formamide (50 mL) was added within 30 min and the reaction was continued for further 4 hours. The reaction mixture was diluted with water (100 mL) and was extracted with ethyl acetate (3×100 mL), washed with water (3×100 mL), brine (200 mL), and was dried over sodium sulfate. The solvent was evaporated under reduced pressure, to yield the title compound.

Workup

  1. additionwas added
  2. temperaturewarmed to 90° C. to 95° C
  3. additionwas added within 30 min
  4. extractionwas extracted with ethyl acetate (3×100 mL)
  5. washwashed with water (3×100 mL), brine (200 mL)
  6. dry with materialwas dried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c555ed21055b47cf8557ee44b7ab1336
Source dataset
uspto-grants-2006_01
Patent number
US06987123B2

Reaction notes

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