Aniline → 4'-Methylbenzanilide

HRID 1789655

Reaction equation

HRID 1789655 reaction equation
Cl[CH2:2]Cl.[NH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:11]1(C)[CH:16]=[CH:15][C:14]([C:17](Cl)=[O:18])=[CH:13][CH:12]=1>CCOCC>[CH3:2][C:8]1[CH:9]=[CH:10][C:5]([NH:4][C:17](=[O:18])[C:14]2[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 6344DichloromethaneHCID 134054-Methylbenzoyl Chloride

Product 1

HCID 684974'-Methylbenzanilide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 0° C. dichloromethane (300 mL) solution of 25 mL (274 mmol) of aniline was added 16 mL (123 mmol) para-toluoyl chloride over 10 min. The mixture was stirred at room temperature for 0.5 h, treated with 200 mL of ether and filtered immediately. The filtrate was washed with 1 M HCl (2×50 mL), 0.1 M NaOH (2×50 mL), and saturated aqueous ammonium chloride, dried over Na2SO4 and concentrated. Para-methylbenzanilide (17.3 g) was obtained as a tan solid and used directly.

Workup

  1. filtrationfiltered immediately
  2. washThe filtrate was washed with 1 M HCl (2×50 mL), 0.1 M NaOH (2×50 mL), and saturated aqueous ammonium chloride
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4706a63b928d4b74b43d4d6ac8d84992
Source dataset
uspto-grants-2006_07
Patent number
US07071177B2

Linked notes

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