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

HRID 1457660Notes

Reaction equation

HRID 1457660 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.[Cl-].[C:22]1([CH2:28][C:29]2[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=2[C:31](Cl)=[O:32])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[C:22]1([CH2:28][C:29]2[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=2[C:31]([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:32])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 4

HCID 312ChlorideHCID 12082Methyl 4-aminobenzoateHCID 81531DiisopropylethylamineHCID 126823622-Benzylbenzoyl chloride

Product 1

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

Procedure

To 3.03 g of methyl 4-aminobenzoate and 3.12 g of N,N-diisopropylethylamine in 75 ml of methylene to 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(Na2 SO4). 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. additionadded to the filtrate at the boil

Sources & evidence

ORD record
ord-570735a8d6f549c397b27f93e1717201
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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