Water → HCID 57883340, compound

HRID 1817918Notes

Reaction equation

HRID 1817918 reaction equation
[CH3:1][Si:2]([CH3:13])([CH3:12])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11].[Br:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[Br:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([NH:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH2:4][CH2:3][Si:2]([CH3:12])([CH3:1])[CH3:13])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 235422-Bromobenzoyl chlorideHCID 57883359HCID 57883359, compound

Product 1

HCID 57883340HCID 57883340, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

425 mg of 2-(2-trimethylsilylethyl)phenylamine (2.2 mmol) and 438 mg (2.0 mmol) of 2-bromo-benzoyl chloride were dissolved in 20 ml of acetonitrile, and 332 mg (2.4 mmol) of potassium carbonate were added. The reaction mixture was stirred at room temperature for 18 h, 20 ml of water were then added, the mixture was extracted with ethyl acetate and the extract was dried over sodium sulphate. Removal of the solvent and column-chromatographic purification on silica gel 60 (mobile phase: methylene chloride) gave 405 mg (54% of theory) of 2-bromo-N-[2-(2-trimethylsilyl-ethyl)phenyl]benzamide [log P (pH 2.3)=4.32].

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialthe extract was dried over sodium sulphate
  3. customRemoval of the solvent and column-chromatographic purification on silica gel 60 (mobile phase: methylene chloride)

Sources & evidence

ORD record
ord-b35aed3960304e46b8c5bbe6199728af
Source dataset
uspto-grants-2009_10
Patent number
US07598389B2

Reaction notes

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