Water → HCID 18182246, compound

HRID 1359410Notes

Reaction equation

HRID 1359410 reaction equation
[C:1]([C:9]1[CH:13]=[CH:12][S:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:14]N1C(=O)CCC1=O.O>CN(C)C(=O)C.C(O)(=O)C>[C:1]([C:9]1[CH:13]=[C:12]([Br:14])[S:11][CH:10]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 2486473-BENZOYLTHIOPHENE

Product 1

HCID 18182246HCID 18182246, compoundYield 63.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 31374DimethylacetamideSolvent

Procedure

3.0 g of 3-benzoylthiophene was dissolved in 10 ml of N,N-dimethylacetamide and 1 ml of acetic acid, and 2.83 g of N-bromosuccinimide was added thereto, followed by stirring overnight. Water was added to the reaction solution, followed by extracting with diethyl ether. The extract was washed with an aqueous saturated sodium bicarbonate solution, dried over anhydrous magnesium and then evaporated. The residue was subjected to silica gel column chromatography and eluted with 10% ethyl acetate/hexan, to give 2.7 g of the target compound.

Workup

  1. extractionby extracting with diethyl ether
  2. washThe extract was washed with an aqueous saturated sodium bicarbonate solution
  3. dry with materialdried over anhydrous magnesium
  4. customevaporated
  5. washeluted with 10% ethyl acetate/hexan

Sources & evidence

ORD record
ord-3e974fc0ab3a433882ecf36825c409fc
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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