N-bromobutanimide → HCID 19347979, compound

HRID 1637186Notes

Reaction equation

HRID 1637186 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:11]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:12]=2[S:13][C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]>ClC(Cl)(Cl)Cl>[Br:1][CH2:24][C:21]1[CH:22]=[CH:23][C:11]2[C:10]([Cl:9])=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[S:13][C:12]=2[CH:20]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 4343151HCID 4343151, compound

Product 1

HCID 19347979HCID 19347979, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Catalytic azobisisobutylnitrile (AIBN, 0.28 g) and N-bromosuccinimide (4.8 g, 26.8 mmol) were added to a solution of ethyl 3-chloro-6-methylbenzo[b]thiophene-2-carboxylate (Preparation 9, 6.5 g, 25.5 mmol) in tetrachloromethane (50 ml), under a nitrogen atmosphere. The mixture was heated to reflux for 5 hours, cooled, and then loaded onto a silica gel column. The product was eluted with a gradient mixture of dichloromethane and hexane (initially 30:70 increasing to 50:50, and then 70:30). The solvent was removed under reduced pressure to leave the title compound as a colourless solid (8.7 g)

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 hours
  3. temperaturecooled
  4. washThe product was eluted with a gradient mixture of dichloromethane and hexane (initially 30:70 increasing to 50:50
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cf04f4bef04f41d2b31308bcf885683d
Source dataset
uspto-grants-2000_03
Patent number
US06040309

Reaction notes

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