N-bromobutanimide → HCID 70144068, compound

HRID 1281686Notes

Reaction equation

HRID 1281686 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[N:11]1[C:15]2[CH:16]=[C:17]([Cl:21])[C:18]([Cl:20])=[CH:19][C:14]=2[N:13]=[CH:12]1)(=[O:3])[CH3:2].[Br:22]N1C(=O)CCC1=O>O1CCCC1.C(Cl)(Cl)Cl>[C:1]([O:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[N:11]1[C:15]2[CH:16]=[C:17]([Cl:21])[C:18]([Cl:20])=[CH:19][C:14]=2[N:13]=[C:12]1[Br:22])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 70145021HCID 70145021, compound

Product 1

HCID 70144068HCID 70144068, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

(±)-Trans-2-(5,6-dichloro-1H-benzimidazol-1-yl)cyclohexyl acetate (part b of this example, 6.62 g, 20.2 mmol) in tetrahydrofuran (120 ml) was refluxed while N-bromosuccinimide (7.20 g, 40.5 mmol) was added in one portion. Reflux was continued for 10 minutes. The solution was cooled and diluted with chloroform (200 ml). The chloroform solution was extracted with aqueous sodium bicarbonate, then water, and dried (sodium sulfate). Evaporation of volatiles in vacuo left white crystals, after trituration from ethyl acetate-hexanes (5.77 g, 70%), m.p. 167-169° C.

Workup

  1. additionwas added in one portion
  2. temperatureReflux
  3. temperatureThe solution was cooled
  4. extractionThe chloroform solution was extracted with aqueous sodium bicarbonate
  5. dry with materialwater, and dried (sodium sulfate)
  6. customEvaporation of volatiles in vacuo
  7. waitleft white crystals

Sources & evidence

ORD record
ord-3efe8d6a1d974ebabd9f74e1537bf6a0
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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