N-bromobutanimide → HCID 54404171, compound

HRID 1734642Notes

Reaction equation

HRID 1734642 reaction equation
[C:1]([O:4][CH:5]1[CH:9]([N:10]2[C:14]3[CH:15]=[C:16]([Cl:20])[C:17]([Cl:19])=[CH:18][C:13]=3[N:12]=[CH:11]2)[CH2:8][CH:7]([CH2:21][O:22][C:23](=[O:25])[CH3:24])[CH:6]1[O:26][C:27](=[O:29])[CH3:28])(=[O:3])[CH3:2].[Br:30]N1C(=O)CCC1=O>O1CCOCC1>[C:1]([O:4][CH:5]1[CH:9]([N:10]2[C:14]3[CH:15]=[C:16]([Cl:20])[C:17]([Cl:19])=[CH:18][C:13]=3[N:12]=[C:11]2[Br:30])[CH2:8][CH:7]([CH2:21][O:22][C:23](=[O:25])[CH3:24])[CH:6]1[O:26][C:27](=[O:29])[CH3:28])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 54044812HCID 54044812, compound

Product 1

HCID 54404171HCID 54404171, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(±)(1R*, 2S*, 3S*, 5S*)-3-(Acetoxymethyl)-5-(5,6-dichloro-1H-benzimidazol-1-yl)-1,2-cyclopentanediyl diacetate (4.20 g, 9.48 mmol) was refluxed in dry dioxane (25 mL) while freshly recrystallized N-bromosuccinimide (3.37 g, 18.9 mmol) was added all at once. After 5 minutes of reflux, volatiles were removed in vacuo. The residue was partitioned between water and chloroform. The chloroform layer was dried (sodium sulfate), and evaporated to an oil which was chromatographed on silica gel with elution by 1:1 hexanes-ethyl acetate. Resolidification from ethanol-water gave title compound as white powder (3.10 g, 63%), m.p. 157°-158.5° C.; 1H-NMR(DMSO-d6) identical to that of the sample described in Example 3.

Workup

  1. additionwas added all at once
  2. temperatureAfter 5 minutes of reflux
  3. customvolatiles were removed in vacuo
  4. customThe residue was partitioned between water and chloroform
  5. dry with materialThe chloroform layer was dried (sodium sulfate)
  6. customevaporated to an oil which
  7. customwas chromatographed on silica gel with elution by 1:1 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-0cce157a4a0440a49b8b8a62b73222ad
Source dataset
uspto-grants-1996_07
Patent number
US05534535

Reaction notes

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