Benzoyl chloride → Ethyl 3-benzamidobenzoate

HRID 2086761Notes

Reaction equation

HRID 2086761 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(N(CC)CC)C.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(OCC)(=O)C>ClCCl.O>[C:20]([NH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11400Ethyl 3-aminobenzoate

Product 1

HCID 670250Ethyl 3-benzamidobenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of ethyl 3-aminobenzoate (996 mg) and triethylamine (0.85 ml) in dichloromethane (10 ml) was added benzoyl chloride (0.70 ml). The mixture was stirred at room temperature for 15 minutes, poured into a mixture of ethyl acetate and water. The organic phase was washed with brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give ethyl 3-benzoylaminobenzoate (1.36 g).

Workup

  1. washThe organic phase was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe resultant solid was collected
  5. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-f66a0dce71c5435fa02422901105ac64
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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