Benzoyl chloride → HCID 19744583, compound

HRID 2254428Notes

Reaction equation

HRID 2254428 reaction equation
CO[CH:3]([O:11]C)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[CH:5]=1.[OH-].[Na+].[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1.O>[C:15]([NH:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[CH:3]=[O:11])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 2325713-(dimethoxymethyl)aniline

Product 1

HCID 19744583HCID 19744583, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

1.06 g of 3-aminobenzaldehyde dimethyl acetal was dissolved in a mixture of 5 ml of toluene and 10 ml of water containing 0.8 g of sodium hydroxide, and 5 ml of a toluene solution of 1.3 g of benzoyl chloride was added. The mixture was stirred at room temperature for 2 hours. The organic layer was separated, and evaporated under reduced pressure. The residue was dissolved in a mixture of 10 ml of methanol and 10 ml of 10% hydrochloric acid, and heated at 90° C. for 30 minutes. Water (20 ml) was added to the reaction mixture to allow it to cool. There was obtained 1.16 g (yield 87.3%) of 3-benzoylaminobenzaldehyde as colorless needles having a melting point of 122° to 123° C.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. customevaporated under reduced pressure
  4. dissolutionThe residue was dissolved in a mixture of 10 ml of methanol and 10 ml of 10% hydrochloric acid
  5. temperatureheated at 90° C. for 30 minutes
  6. additionWater (20 ml) was added to the reaction mixture
  7. temperatureto cool

Sources & evidence

ORD record
ord-7fe8b96733cb4b6c9cec21a19597e21d
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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