Bicarbonate Ion → 2-[bis(4-hydroxyphenyl)methyl]-N-(2,4-dimethoxyphenyl)benzamide

HRID 36439Notes

Reaction equation

HRID 36439 reaction equation
C(=O)([O-])O.CO.C([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([C:37]2[CH:42]=[CH:41][C:40]([O:43]C(=O)C)=[CH:39][CH:38]=2)[C:18]2[CH:36]=[CH:35][CH:34]=[CH:33][C:19]=2[C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=2[O:31][CH3:32])=[O:21])=[CH:13][CH:12]=1)(=O)C>[Na]>[OH:43][C:40]1[CH:41]=[CH:42][C:37]([CH:17]([C:14]2[CH:13]=[CH:12][C:11]([OH:10])=[CH:16][CH:15]=2)[C:18]2[CH:36]=[CH:35][CH:34]=[CH:33][C:19]=2[C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=2[O:31][CH3:32])=[O:21])=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 769Bicarbonate IonHCID 887MethanolHCID 152967812-[Bis(4-acetoxyphenyl)methyl]-N-(2,4-dimethoxyphenyl)benzamide

Product 1

HCID 152967822-[bis(4-hydroxyphenyl)methyl]-N-(2,4-dimethoxyphenyl)benzamideYield 56%

Reagents, catalysts & solvents 1

HCID 5360545SodiumSolvent

Procedure

In a mixture of 50 ml of saturated aqueous sodium. hydrogencarbonate solution and 50 ml of methanol was suspended 2.6 g of Compound 2 prepared in Example 1, and the suspension was heated under reflux for 30 minutes. The resulting mixture was concentrated under reduced pressure, and water was added to the residue. The resulting mixture was extracted with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was recrystallized to afford 1.23 g of the desired product.

Workup

  1. temperaturethe suspension was heated
  2. temperatureunder reflux for 30 minutes
  3. concentrationThe resulting mixture was concentrated under reduced pressure, and water
  4. additionwas added to the residue
  5. extractionThe resulting mixture was extracted with ethyl acetate
  6. dry with materialthe extract was dried over anhydrous magnesium sulfate
  7. concentrationAfter concentration under reduced pressure
  8. customthe residue was recrystallized

Sources & evidence

ORD record
ord-6029f0ddbc5f49ef962aebcb76173fc8
Source dataset
uspto-grants-1995_05
Patent number
US05413997

Reaction notes

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