Water → HCID 86232766, compound

HRID 1012409Notes

Reaction equation

HRID 1012409 reaction equation
[CH3:1][C:2]1[N:3]([S:9]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])[CH:4]=[CH:5][C:6]=1[CH:7]=[O:8].[Br:18]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:18][C:4]1[N:3]([S:9]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)(=[O:10])=[O:11])[C:2]([CH3:1])=[C:6]([CH:7]=[O:8])[CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 86232756HCID 86232756, compound

Product 1

HCID 86232766HCID 86232766, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (974 mg) in N,N-dimethylformamide (10 mL) was added N-bromosuccinimide (1.17 g) at 0° C., and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=2:1) to give the title compound as white crystals (yield 675 mg, 53%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=2:1)

Sources & evidence

ORD record
ord-ffb80a7f76894e4d9405f93014c5c87b
Source dataset
uspto-grants-2011_07
Patent number
US07977488B2

Reaction notes

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