Benzocaine → HCID 954662, compound

HRID 863007Notes

Reaction equation

HRID 863007 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:4]=1[C:5](Cl)=[O:6].[NH2:14][C:15]1[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl.O>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:4]=1[C:5]([NH:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][CH:25]=1)=[O:6]

Participants

7

Reactant 3

HCID 2337BenzocaineHCID 8471TriethylamineHCID 748102,6-Dimethoxybenzoyl chloride

Product 1

HCID 954662HCID 954662, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2 g (10 mmol) of 2,6-dimethoxybenzoyl chloride, 1.65 g (10 mmol) of ethyl 4-aminobenzoate, 1.11 g of triethylamine and 61 mg of 4-dimethylaminopyridine in 10 ml of dichloromethane is refluxed for 20 hours. The mixture is diluted with water and the organic layer separated. The organic layer is washed with water, 1N HCl, 1N Na2CO3, brine and dried (Na2SO4). The solvent is removed to give a solid which is crystallized from ethyl acetate to give 1.22 g of ethyl 4-[(2,6-dimethoxybenzoyl)amino]benzoate as crystals, m.p. 183°-185° C.

Workup

  1. temperatureis refluxed for 20 hours
  2. customthe organic layer separated
  3. washThe organic layer is washed with water, 1N HCl, 1N Na2CO3, brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent is removed
  6. customto give a solid which
  7. customis crystallized from ethyl acetate

Sources & evidence

ORD record
ord-b2c7c695a6b540179657f7cf8c885e75
Source dataset
uspto-grants-1998_02
Patent number
US05719278

Reaction notes

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