Acetyl chloride → Acetamide, N-(2-benzoylphenyl)-

HRID 1789634Notes

Reaction equation

HRID 1789634 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].C(N(CC)CC)C.[C:23]([Cl:26])(=[O:25])[CH3:24]>C(Cl)Cl>[Cl:26][C:23]1[CH:24]=[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]2[C:2](=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:1]=1.[C:23]([NH:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5])(=[O:25])[CH3:24]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 760802-Aminobenzophenone

Product 2

HCID 97474Acetamide, N-(2-benzoylphenyl)-HCID 23066872-Chloro-4-phenylquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Chloro-4-phenylquinoline was prepared by the following method (Rxn-1). 2-Aminobenzophenone (21 g, 106.5 mmol) was dissolved in methylene chloride (213 mL) and triethylamine (22.3 mL, 159.8 mmol) was added slowly. After cooling to 0° C., acetylchloride (8.3 mL, 117.2 mmol) was added to the reaction mixture dropwise. The reaction mixture was then removed from ice and allowed to stir overnight. Upon the addition of 10% hydrochloric acid (84 mL), the aqueous layers were combined and extracted with ethyl acetate. The organic phases were combined, dried with magnesium sulfate, and concentrated. Purification by column chromatography (25% ethyl acetate/heptane) gave 2-acetamidobenzophenone.

Workup

  1. customThe reaction mixture was then removed from ice
  2. additionUpon the addition of 10% hydrochloric acid (84 mL)
  3. extractionextracted with ethyl acetate
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated
  6. customPurification by column chromatography (25% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-587fa6dd1dba43fda10d118c83fddfdf
Source dataset
uspto-grants-2006_07
Patent number
US07070868B2

Reaction notes

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