4-Formylbenzoic acid → HCID 22350017, compound

HRID 896404Notes

Reaction equation

HRID 896404 reaction equation
S(Cl)(Cl)=O.[C:5]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1)([OH:7])=O.[CH2:16]([NH:18][CH3:19])[CH3:17]>ClCCl.CN(C)C=O>[CH2:16]([N:18]([CH3:19])[C:5](=[O:7])[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1)[CH3:17]

Participants

5

Reactant 3

HCID 120884-Formylbenzoic acidHCID 12219N-MethylethylamineHCID 24386Thionyl Chloride

Product 1

HCID 22350017HCID 22350017, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

Thionyl chloride (26 mL, 0.36 mol) was added dropwise to a solution of 4-carboxybenzaldehyde (50.0 g, 0.33 mol) in 2000 mL of dichloromethane:N,N-dimethylformamide (4:1 mixture). The mixture was stirred overnight at room temperature. Ethylmethylamine (75.0 g, 1.3 mol) was added dropwise, and stirring was continued at room temperature for 90 minutes. The solvent was removed under vacuum, the residue was dissolved in 500 mL of 0.1M sodium hydroxide, and extracted with ethyl acetate. The organic phase was washed with water, dried over sodium sulfate and evaporated under vacuum to give 23.8 g (38%) of N-ethyl-4-formyl-N-methylbenzamide as a yellow oil.

Workup

  1. stirringstirring
  2. waitwas continued at room temperature for 90 minutes
  3. customThe solvent was removed under vacuum
  4. dissolutionthe residue was dissolved in 500 mL of 0.1M sodium hydroxide
  5. extractionextracted with ethyl acetate
  6. washThe organic phase was washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-1ad79b92f5d94bd4a8325fd780349321
Source dataset
uspto-grants-2005_07
Patent number
US06919350B2

Reaction notes

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