Diethyl Ether → HCID 22010687, compound

HRID 323140Notes

Reaction equation

HRID 323140 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:41]=[CH:40][C:20]([C:21]([N:23]([CH3:39])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30]C(=O)C4C=CC=CC=4)=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)C>CO.C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([N:23]([CH3:39])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[OH:30])=[O:22])=[CH:40][CH:41]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 22010609HCID 22010609, compound

Product 1

HCID 22010687HCID 22010687, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent2×

Procedure

To a solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-benzoyloxyphenyl)benzamide (350 mg) in methanol (10 ml) was added potassium carbonate (89.5 mg) and the mixture was stirred at ambient temperature overnight. Chloroform was added to the mixture and the solution was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo to give an oil and the oil was subjected to silica gel column (30 g, 1% methanol in chloroform) to give an oil. The oil was solidified with diethyl ether to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-hydroxyphenyl)benzamide (228 mg) as a white powder.

Workup

  1. washthe solution was washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customto give an oil
  5. customto give an oil

Sources & evidence

ORD record
ord-0b5b6874865e4c179a92c0498458b5c7
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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