4-Bromophenacyl bromide → HCID 57481205, compound

HRID 1773629Notes

Reaction equation

HRID 1773629 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=O.Cl.[CH:13]1([C:16](=[NH:18])[NH2:17])[CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[NH:18][C:16]([CH:13]3[CH2:15][CH2:14]3)=[N:17][CH:2]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 11430Potassium CarbonateHCID 2781916Cyclopropanecarboximidamide hydrochloride

Product 1

HCID 57481205HCID 57481205, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 89.0 g (320 mmol) 2-bromo-1-(4-bromophenyl)ethanone in 2.0 L N,N-dimethylformamide were added cyclopropanecarboximidamide hydrochloride, 132.8 g potassium carbonate and the mixture was stirred at 23° C. overnight. After removal of the solvent, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. After filtration and removal of the solvent the residue was purified by crystallisation to give 42.1 g (50%) of the title compound.

Workup

  1. customAfter removal of the solvent, water
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration and removal of the solvent the residue
  7. customwas purified by crystallisation

Sources & evidence

ORD record
ord-63655a7dccda4baca010a59e952a647c
Source dataset
uspto-grants-2016_02
Patent number
US09255100B2

Reaction notes

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