Ethyl bromoacetate → HCID 86756596, compound

HRID 323155Notes

Reaction equation

HRID 323155 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:37]=[CH:36][C:20]([C:21]([N:23]([CH3:35])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH:32]=[N:33][OH:34])=[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+].Br[CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47]>CN(C)C=O.C(OCC)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([N:23]([CH3:35])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH:32]=[N:33][O:34][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])=[O:22])=[CH:36][CH:37]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 73858926HCID 73858926, compound

Product 1

HCID 86756596HCID 86756596, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(2-hydroxyiminoethoxy)phenyl]benzamide (255 mg) and potassium carbonate (78.5 mg) in N,N-dimethylformamide (10 ml) was added ethyl bromoacetate (94.9 mg) and the mixture was stirred at ambient temperature for 5 hours. The mixture was diluted with ethyl acetate (30 ml) and the solution was washed with water and brine. The organic phase was dried over magnesium sulfate and the solvent was evaporated in vacuo to give an oil. The oil was purified by silica gel column (chloroform) to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-[2-(ethoxycarbonylmethoxyimino)ethoxy]phenyl]benzamide (245 mg) as a colorless amorphous.

Workup

  1. washthe solution was washed with water and brine
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customto give an oil
  5. customThe oil was purified by silica gel column (chloroform)

Sources & evidence

ORD record
ord-7a992bc13be64596b0353ac67b2c6427
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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