Water → 1-(3-Benzoylamino-2-oxopropyl)-5-bromo-2-chlorobenzene

HRID 1625889Notes

Reaction equation

HRID 1625889 reaction equation
Cl.[NH2:2][CH2:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[C:10]([Br:12])[CH:9]=[CH:8][C:7]=1[Cl:13].O.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[C:16]([NH:2][CH2:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[C:10]([Br:12])[CH:9]=[CH:8][C:7]=1[Cl:13])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 666088101-(3-Amino-2-oxopropyl)-5-bromo-2-chlorobenzene-hydro-chloride

Product 1

HCID 666074521-(3-Benzoylamino-2-oxopropyl)-5-bromo-2-chlorobenzene

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixed solution of the above 1-(3-amino-2-oxopropyl)-5-bromo-2-chlorobenzene.hydrochloride (1.70 g) in ethyl acetate (30 ml)-water (15 ml) was cooled to 0° C. Added thereto were benzoyl chloride (0.99 ml) and sodium hydrogen carbonate (2.39 g), and the mixture was stirred at the same temperature for 3 hours. The organic layer was washed with brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:ethyl acetate=95:5) to give 1-(3-benzoylamino-2-oxopropyl)-5-bromo-2-chlorobenzene (710 mg) as a colorless solid. APCI-Mass m/Z 366/368 (M+H).

Workup

  1. additionAdded
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform:ethyl acetate=95:5)

Sources & evidence

ORD record
ord-c1dc22a6c6454f0d93b9c738d4053d37
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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