Water → Ethyl 4-[(2-methylbenzoyl)amino]benzoate

HRID 362325

Reaction equation

HRID 362325 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH3:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16](Cl)=[O:17].C(N(CC)CC)C.O>ClCCl>[CH3:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1)=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 2337BenzocaineHCID 8471TriethylamineHCID 702762-Methylbenzoyl chloride

Product 1

HCID 689910Ethyl 4-[(2-methylbenzoyl)amino]benzoateYield 77.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 43.42 g (0.26 mol) of ethyl 4-aminobenzoate and 40.8 g (0.26 mol) of 2-methylbenzoyl chloride in 150 ml of dichloromethane is cooled in an ice bath and 26.56 g (0.26 mol) of triethylamine is added dropwise. After the addition, the solution is stirred at room temperature overnight. The mixture is poured into water and the organic layer separated. The organic layer is washed with water, 1N HCl, 1M NaHCO3 and dried (Na2SO4). The solvent is removed and the solid slurried with ethyl acetate and filtered to give 57 g of ethyl 4-[(2-methylbenzoyl)amino]benzoate as crystals, m.p. 110°-115° C.

Workup

  1. temperatureis cooled in an ice bath
  2. additionAfter the addition
  3. customthe organic layer separated
  4. washThe organic layer is washed with water, 1N HCl, 1M NaHCO3
  5. dry with materialdried (Na2SO4)
  6. customThe solvent is removed
  7. filtrationthe solid slurried with ethyl acetate and filtered

Sources & evidence

ORD record
ord-592d5fcdb688449bb329269df607bd14
Source dataset
uspto-grants-1999_02
Patent number
US05869483

Linked notes

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