Benzoyl chloride → HCID 57879375, compound

HRID 1673345Notes

Reaction equation

HRID 1673345 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[NH2:17][C:18]1[CH:19]=[C:20]([CH:29]=[CH:30][C:31]=1[CH3:32])[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22]>C(Cl)Cl>[C:21]([C:20]1[CH:29]=[CH:30][C:31]([CH3:32])=[C:18]([NH:17][C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:19]=1)(=[O:22])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 106085593-amino-4-methylbenzophenone

Product 1

HCID 57879375HCID 57879375, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.67 mL of triethylamine and 0.34 ml of benzoyl chloride was added to 5 mL of methylene chloride solution containing 0.51 g of 3-amino-4-methylbenzophenone while ice-cooled and stirred at room temperature for 2 hours. The solvent of the reaction mixture was evaporated under reduced pressure and ethyl acetate and 1.0 mol/L hydrochloric acid were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. Hexane and diisopropyl ether were added to the obtained residue and a solid substance was separated by filtration to obtain 0.71 g of N-(5-benzoyl-2-methylphenyl)benzamide as white solid.

Workup

  1. temperaturecooled
  2. customThe solvent of the reaction mixture was evaporated under reduced pressure and ethyl acetate and 1.0 mol/L hydrochloric acid
  3. additionwere added
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. washafter washed with a saturated sodium hydrogen carbonate aqueous solution
  7. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  8. additionHexane and diisopropyl ether were added to the obtained residue
  9. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-7848c1e823ca46c282d3059ddb82982e
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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