Chloroform → HCID 22010844, compound

HRID 323145Notes

Reaction equation

HRID 323145 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:35]=[CH:34][C:20]([C:21]([N:23]([CH3:33])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30](=[O:32])[CH3:31])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].C(Cl)(Cl)Cl>CO>[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]([CH3:33])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH:30]([OH:32])[CH3:31])=[O:22])=[CH:34][CH:35]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 22010972HCID 22010972, compound

Product 1

HCID 22010844HCID 22010844, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-acetylphenyl)benzamide (200 mg) in methanol (15 ml) was added sodium borohydride (16.4 mg) and the solution was stirred at ambient temperature for 3 hours. Chloroform was added to the mixture and the solution was washed successively with water and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo to give a syrup and the crude product was purified by silica gel column (chloroform) to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(1-hydroxyethyl)phenyl]-benzamide (150 mg) as a white solid.

Workup

  1. washthe solution was washed successively with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customto give a syrup
  5. customthe crude product was purified by silica gel column (chloroform)

Sources & evidence

ORD record
ord-85d4a1e793604e9aa14a87a7955dc3be
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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