Hydrogen Bromide → HCID 18756149, compound

HRID 433920Notes

Reaction equation

HRID 433920 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[BrH:20].BrBr>C(O)(=O)C>[NH2:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([Br:20])[C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:13])=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 222857924-(2-Oxo-2-phenylethyl)benzene-1-sulfonamide

Product 1

HCID 18756149HCID 18756149, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a mixture of 14.4 g (52 mmol) of 2-(4-aminosulfonylphenyl)-1-phenylethanone in 240 mL of glacial acetic acid stirred under nitrogen, a solution of 24 mL of hydrobromic acid in glacial acetic acid (33%) was added. To the reaction mixture was added slowly 8.4 g (52 mmol) of bromine. It was stirred at room temperature until complete loss of the colour. After concentration, the resulting residue was dissolved in ethyl acetate (500 mL). The organic layer was washed twice with 5% aqueous sodium bicarbonate solution (2×350 mL) and with brine (350 mL). The organic layer was dried, filtered and concentrated in vacuum. The residue was swished in hexane to give 14.9 g (80%) of the desired solid as a white powdered solid.

Workup

  1. stirringIt was stirred at room temperature until complete loss of the colour
  2. concentrationAfter concentration
  3. dissolutionthe resulting residue was dissolved in ethyl acetate (500 mL)
  4. washThe organic layer was washed twice with 5% aqueous sodium bicarbonate solution (2×350 mL) and with brine (350 mL)
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-d075e444edbd4641b8a3e85e9a16c4fb
Source dataset
uspto-grants-2003_12
Patent number
US06670365B1

Reaction notes

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