Benzoyl chloride → Benzamide, N-(4-aminophenyl)-

HRID 2233223Notes

Reaction equation

HRID 2233223 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]1([NH2:17])[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1.C(N(CC)CC)C>ClCCl>[C:1]([NH:16][C:13]1[CH:14]=[CH:15][C:10]([NH2:17])=[CH:11][CH:12]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 7814P-PhenylenediamineHCID 8471Triethylamine

Product 1

HCID 87196Benzamide, N-(4-aminophenyl)-Yield 28.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzoyl chloride (10.7 ml, 92.5 mmol) was added to a stirred solution of 1,4-phenylenediamine (10.0 g, 92.5 mmol) and triethylamine (14.2 ml, 102 mmol) in dichloromethane (250 ml) at 0° C. The reaction was allowed to warm to ambient temperature over 3 hours, the solid was filtered off and water (100 ml) was added to the filtrate, causing precipitation of a second solid. Collection of this solid by suction filtration and drying in vacuo yielded N-benzoyl 4-aminoaniline (5.55 g, 28% yield) as a white solid:

Workup

  1. filtrationthe solid was filtered off
  2. additionwater (100 ml) was added to the filtrate
  3. customprecipitation of a second solid
  4. customCollection of this solid
  5. filtrationby suction filtration
  6. customdrying in vacuo

Sources & evidence

ORD record
ord-0209add147794d3397babdc729c32287
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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