Potassium Carbonate → 4-bromo-N-(2,2-dimethoxyethyl)benzamide

HRID 452875Notes

Reaction equation

HRID 452875 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][CH:9]([O:12][CH3:13])[CH2:10][NH2:11].[Br:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1>O.CC(C)=O>[Br:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:11][CH2:10][CH:9]([O:12][CH3:13])[O:8][CH3:7])=[O:20])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 685154-Bromobenzoyl chlorideHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 111299414-bromo-N-(2,2-dimethoxyethyl)benzamide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

Potassium carbonate (8.0 g) was added to a solution of 2,2-dimethoxyethylamine in water (90 ml) and acetone (40 ml) at rt. The reaction mixture was cooled in an ice-water bath and 4-bromobenzoyl chloride (16.4 g) dissolved in acetone (70 ml) was added drop-wise over 90 min. The stirred reaction mixture was allowed to warm to rt. After a further 2 h the reaction mixture was extracted into EtOAc (3×75 ml), the combined organics were washed with saturated aqueous sodium hydrogen carbonate, dried (MgSO4) and evaporated to give the amide as an off white solid (18.5 g). LCMS electrospray (+ve) 289 (MH+).

Workup

  1. temperatureThe reaction mixture was cooled in an ice-water bath
  2. additionwas added drop-wise over 90 min
  3. customThe stirred reaction mixture
  4. extractionAfter a further 2 h the reaction mixture was extracted into EtOAc (3×75 ml)
  5. washthe combined organics were washed with saturated aqueous sodium hydrogen carbonate
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-b6232cc56ae349d0a8a38ae58b03b78f
Source dataset
uspto-grants-2013_07
Patent number
US08492375B2

Reaction notes

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