N-bromobutanimide → 5-Bromo-4-methoxythiophene-2-sulfonamide

HRID 1297168Notes

Reaction equation

HRID 1297168 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:8]([NH2:11])(=[O:10])=[O:9])[S:6][CH:7]=1.[Br:12]N1C(=O)CCC1=O>C(Cl)Cl>[Br:12][C:7]1[S:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 15669338HCID 15669338, compound

Product 1

HCID 220195295-Bromo-4-methoxythiophene-2-sulfonamideYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 4-methoxythiophene-2-sulfonamide (240 mg, 1.24 mmol) in CH2Cl2 (40 mL) is added N-bromosuccinimide (287 mg, 1.61 mmol). The reaction mixture is stirred at 0° C. for 7 hr. After 7 hr, the reaction mixture is diluted with CH2Cl2 (150 mL). The organic layer is washed with brine then dried (Na2SO4), filtered and concentrated in vacuo. The crude product is chromatographed on silica gel, eluting with Hex:EtOAc (2:1) to afford the title compound (277 mg, 82%).

Workup

  1. waitAfter 7 hr
  2. washThe organic layer is washed with brine
  3. dry with materialthen dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product is chromatographed on silica gel
  7. washeluting with Hex

Sources & evidence

ORD record
ord-fc39981fd2ac4903b40fa8d59f58fa2d
Source dataset
uspto-grants-2007_07
Patent number
US07250430B2

Reaction notes

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