Methyl 4-aminobenzoate → Methyl 4-[[2-(Phenylmethyl)benzoyl]amino]benzoate

HRID 976398Notes

Reaction equation

HRID 976398 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[C:21]1([CH2:27][C:28]2[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=2[C:30](Cl)=[O:31])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[C:21]1([CH2:27][C:28]2[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=2[C:30]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)=[O:31])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 12082Methyl 4-aminobenzoateHCID 81531DiisopropylethylamineHCID 126823622-Benzylbenzoyl chloride

Product 1

HCID 8765094Methyl 4-[[2-(Phenylmethyl)benzoyl]amino]benzoateYield 72.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3.03 g of methyl 4-aminobenzoate and 3.12 g of N,N-diisopropylethylamine in 75 ml of methylene chloride is added 5.54 g of 2-(phenylmethyl)benzoyl chloride and the reactants stirred at room temperature for 18 hours. The reaction mixture is washed with water, saturated aqueous NaHCO3 and the organic layer dried (Na2SO4). The organic layer is passed through hydrous magnesium silicate two times and hexane added to the filtrate at the boil to give 5.04 g of the desired product as a crystalline solid, m.p. 138°-139° C.

Workup

  1. washThe reaction mixture is washed with water, saturated aqueous NaHCO3
  2. dry with materialthe organic layer dried (Na2SO4)
  3. additionadded to the filtrate at the boil

Sources & evidence

ORD record
ord-f607d2dba835425d9d62b4e152ee44a2
Source dataset
uspto-grants-1997_03
Patent number
US05612334

Reaction notes

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