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

HRID 3496
Notes
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Reaction equation

HRID 3496 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 2337BenzocaineHCID 8471TriethylamineHCID 702762-Methylbenzoyl chloride

Product 1

HCID 689910Ethyl 4-[(2-methylbenzoyl)amino]benzoateYield 76.5%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

A mixture of 43.42 g of ethyl 4-aminobenzoate and 40.8 g of 2-methylbenzoyl chloride in 150 ml of dichloromethane is cooled in an ice bath and 26.56 g of triethylamine the solution is stirrer 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 over 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. A mixture of 50.7 g of the preceding compound in 280 ml of ethyl alcohol and 55 ml of 10N NaOH is refluxed for 5 minutes. The mixture is cooled to room temperature, diluted with 200 ml of water and acidified with concentrated hydrochloric acid (pH 1-2). The mixture is filtered and the solid washed with water and dried to give 51 g of the desired product as white crystals, m.p. 270°-275° C.

Workup

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

Sources & evidence

ORD record
ord-487ac92980e343ec8d41d66e51566ec1
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05733905

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes