N-bromobutanimide → HCID 66729043, compound

HRID 2056729Notes

Reaction equation

HRID 2056729 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([C:10]#[N:11])[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[Br:12]N1C(=O)CCC1=O>CN(C=O)C.O>[Br:12][C:3]1[C:4]2[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][C:5]=2[S:1][CH:2]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 21816574Benzo[b]thiophene-6-carbonitrile

Product 1

HCID 66729043HCID 66729043, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-benzothiophene-6-carbonitrile (2.13 g, 13.4 mmol) in dry DMF (20 mL) at −10° C. was added freshly recrystallised N-bromosuccinimide (2.38 g, 13.4 mmol). The solution was allowed to warm to room temperature and stirred over the weekend. The mixture was diluted with water and extracted into diethyl ether, and the organic extract washed with water, then brine. The extracts were dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by flash chromatography on silica, eluting with ethyl acetate/hexane (1:9), to yield the title compound as a white solid.

Workup

  1. extractionextracted into diethyl ether
  2. extractionthe organic extract
  3. washwashed with water
  4. dry with materialThe extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude product was purified by flash chromatography on silica
  8. washeluting with ethyl acetate/hexane (1:9)

Sources & evidence

ORD record
ord-7ac78351942046b29770a41e6de5c8e3
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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