Water → HCID 22141415, compound

HRID 1787865Notes

Reaction equation

HRID 1787865 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:7]=[C:8]([Cl:10])[CH:9]=1)(=[O:3])[CH3:2].[Br:16]Br.O>O1CCOCC1>[Br:16][CH2:2][C:1]([C:4]1[CH:5]=[C:6]([NH:11][S:12]([CH3:15])(=[O:13])=[O:14])[CH:7]=[C:8]([Cl:10])[CH:9]=1)=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 22141380HCID 22141380, compound

Product 1

HCID 22141415HCID 22141415, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

N-(3-acetyl-5-chlorophenyl)methanesulfonamide (500 mg) was dissolved in dioxane (10 mL). The temperature was maintained at 50° C. and bromine (0.11 mL) was added. After stirring for 30 minutes, water (50 mL) was added to the mixture, and the mixture was extracted with ethyl acetate (50 mL). The ethyl acetate layer was washed with water (50 mL) twice and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (1:2 ethyl acetate/hexane) to yield N-(3-bromoacetyl-5-chlorophenyl)methanesulfonamide (600 mg) as a colorless crystal.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (50 mL)
  2. washThe ethyl acetate layer was washed with water (50 mL) twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (1:2 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-167ee1b3ddf04ba79ea3dfdb6e0c7ce9
Source dataset
uspto-grants-2009_03
Patent number
US07511069B2

Reaction notes

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