Benzoyl chloride → HCID 20283403, compound

HRID 463446

Reaction equation

HRID 463446 reaction equation
[CH2:1]([NH:9][C:10](=[O:19])[CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[OH:12])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:20](Cl)(=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>N1C=CC=CC=1>[CH2:1]([NH:9][C:10](=[O:19])[CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[O:12][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 9992529Benzeneacetamide,a-hydroxy-n-(2-phenylethyl)-

Product 1

HCID 20283403HCID 20283403, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-phenethyl mandelic amide 51 g is dissolved in 200 ml of pyridine, and benzoyl chloride 42 ml is added with stirring. Exothermic benzoylation takes place immediately and the reaction mixture is cooled externally with a cold water bath. The stirring is continued for 5 hours, and the reaction mixture is mixed with 1 liter of ice water. The product is extracted with 250 ml of chloroform, washed with 300 ml of 5% sodium bicarbonate, followed by 300 ml of 0.5N HCL and is dried over anhydrous sodium sulfate. On evaporation of chloroform a crystalline product is obtained. The crystals are washed with n-hexane and dried. The yield is 85 g.

Workup

  1. temperaturethe reaction mixture is cooled externally with a cold water bath
  2. extractionThe product is extracted with 250 ml of chloroform
  3. washwashed with 300 ml of 5% sodium bicarbonate
  4. dry with materialis dried over anhydrous sodium sulfate
  5. customOn evaporation of chloroform a crystalline product
  6. customis obtained
  7. washThe crystals are washed with n-hexane
  8. customdried

Sources & evidence

ORD record
ord-a54a3e16cecc45ed8319b72adc3aaa04
Source dataset
uspto-grants-1985_05
Patent number
US04518789

Linked notes

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