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

HRID 962490

Reaction equation

HRID 962490 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-215f3ad8d4c846b9bb8200f7badab585
Source dataset
uspto-grants-1998_06
Patent number
US05760031

Linked notes

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