Benzoyl chloride → HCID 669106, compound

HRID 922545Notes

Reaction equation

HRID 922545 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.[C:10](Cl)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1C=CC=CC=1>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([CH3:9])[CH:3]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 114234-Bromo-2-methylaniline

Product 1

HCID 669106HCID 669106, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-bromo-2-methylaniline (3.55 g) in pyridine (95 mL) was added benzoyl chloride (2.66 mL). The mixture was stirred at room temperature for 1 hr and the solvent was evaporated under reduced pressure. To the residue was added 2N hydrochloric acid. The mixture was extracted with ethyl acetate, and the extract was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was washed with diisopropyl ether to give the title compound (4.35 g).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionTo the residue was added 2N hydrochloric acid
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-f01791682e7a492ba6b2a2c26c7ff7b1
Source dataset
uspto-grants-2016_03
Patent number
US09278931B2

Reaction notes

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