N-bromobutanimide → HCID 15407222, compound

HRID 1609034Notes

Reaction equation

HRID 1609034 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H: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][C@@H:7]([CH2:21][O:22][C:23](=[O:25])[CH3:24])[C@@H: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][C@@H:5]1[C@@H: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][C@@H:7]([CH2:21][O:22][C:23](=[O:25])[CH3:24])[C@@H:6]1[O:26][C:27](=[O:29])[CH3:28])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 15280846HCID 15280846, compound

Product 1

HCID 15407222HCID 15407222, 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 hexanesoethyl 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 hexanesoethyl acetate

Sources & evidence

ORD record
ord-1f5730748fef4a15bd597e0856fad66d
Source dataset
uspto-grants-1995_03
Patent number
US05399580

Reaction notes

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