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Sodium Bicarbonate → N-(2-hydroxyethyl)-3-methoxy-N-(2-methoxyphenyl)benzamide

HRID 2463
Notes
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Reaction equation

HRID 2463 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[C:6]([N:8]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:24][CH3:25])[CH2:9][CH2:10][O:11]C1CCCCO1)=[O:7].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CO>[OH:11][CH2:10][CH2:9][N:8]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:24][CH3:25])[C:6](=[O:7])[C:5]1[CH:26]=[CH:27][CH:28]=[C:3]([O:2][CH3:1])[CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 539260843-Methoxy-N-(2-methoxyphenyl)-N-(2-tetrahydropyranyloxyethyl)benzamide

Product 1

HCID 19689855N-(2-hydroxyethyl)-3-methoxy-N-(2-methoxyphenyl)benzamideYield 86.8%

Reagents, catalysts & solvents 1

HCID 887Methanol
Solvent

Procedure

3-Methoxy-N-(2-methoxyphenyl)-N-(2-tetrahydropyranyloxyethyl)benzamide (501 mg, 1.30 mmol) was dissolved in methanol (4 ml) to which was subsequently added a catalytically effective amount of p-toluenesulfonic acid monohydrate and stirred for 3 hours at room temperature. The reaction solution was mixed with saturated sodium bicarbonate aqueous solution (10 ml) and extracted with ether, and then washed with water and saturated brine. The resulting organic layer was dried on anhydrous magnesium sulfate, the solvent was removed by evaporation and then the resulting colorless oily residue was purified by subjecting it to a silica gel column chromatography (ether:hexane=3:1) to obtain 340 mg (86.8%) of the title compound in the form of light yellow oil.

Workup

  1. extractionextracted with ether
  2. washwashed with water and saturated brine
  3. dry with materialThe resulting organic layer was dried on anhydrous magnesium sulfate
  4. customthe solvent was removed by evaporation
  5. customthe resulting colorless oily residue was purified

Sources & evidence

ORD record
ord-cbf5b75d0c184a8f8de856d128b7a42f
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05728835

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes