N-Bromosuccinamide → HCID 58521825, compound

HRID 2390284Notes

Reaction equation

HRID 2390284 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1.[Br:18]NC(=O)CCC(N)=O>S(=O)(=O)(O)O>[Br:18][C:3]1[C:2]([CH3:1])=[CH:7][C:6]([NH:8][C:9](=[O:11])[CH3:10])=[C:5]([S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])[CH:4]=1

Participants

4

Reactant 2

HCID 9834204N-BromosuccinamideHCID 58521962HCID 58521962, compound2×

Product 1

HCID 58521825HCID 58521825, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of N-[5-methyl-2-(propylsulfonyl)phenyl]acetamide (Intermediate 229; 5.0 g, 20 mmol) in conc. sulphuric acid (25 ml) was treated in portions with N-bromosuccinamide (3.8 g, 22 mmol). Reaction mixture was stirred at RT for 18 hrs, carefully quenched on ice and extracted to DCM (100 ml). The organic layer was washed with water and brine, dried over sodium sulphate and concentrated. The crude product was purified by column chromatography (silica) eluting with petroleum ether/ethyl acetate to afford the title compound as a white solid.

Workup

  1. customReaction mixture
  2. customcarefully quenched on ice
  3. extractionextracted to DCM (100 ml)
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (silica)
  8. washeluting with petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-ab633dd30ebf4cd6845f09fbe052970c
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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