Imidazole → 2-Cyclopropyl-7-(l iodomethylbut-3-enyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17587Notes

Reaction equation

HRID 17587 reaction equation
N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:25]I.[CH:27]1([C:30]2[O:31][C:32]3[C:33](=[C:35]([C:52]#[N:53])[C:36]([CH3:51])=[C:37]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[C:38]=3[CH:39]([CH2:43]O)[CH2:40][CH:41]=[CH2:42])[N:34]=2)[CH2:29][CH2:28]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1C=CC=CC=1>[CH:27]1([C:30]2[O:31][C:32]3[C:33](=[C:35]([C:52]#[N:53])[C:36]([CH3:51])=[C:37]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[C:38]=3[CH:39]([CH2:43][I:25])[CH2:40][CH:41]=[CH2:42])[N:34]=2)[CH2:29][CH2:28]1

Participants

7

Reactant 5

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 24477Sodium ThiosulfateHCID 685849552-Cyclopropyl-7-(1-hydroxymethylbut-3-enyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 685847562-Cyclopropyl-7-(l iodomethylbut-3-enyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileYield 80.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Imidazole (321 mg, 4.71 mmol), triphenyl phosphine (1.235 g, 4.71 mmol) and then iodine (956 mg, 3.77 mmol) were added to a solution of 2-cyclopropyl-7-(1-hydroxymethylbut-3-enyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-297) (675 mg, 1.88 mmol) dissolved in benzene (20 ml). The solution was stirred under nitrogen atmosphere at room temperature for 20 hours, then aqueous saturated sodium thiosulfate solution was added, followed by stirring at the same temperature for 10 minutes. The aqueous layer was separated, this was extracted three times with ethyl acetate. The organic layers were combined, washed with saturated brine, then dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=19:1, v/v) to obtain the entitled compound (707 mg, 80%).

Workup

  1. stirringby stirring at the same temperature for 10 minutes
  2. customThe aqueous layer was separated
  3. extractionthis was extracted three times with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe insoluble matter was separated by filtration
  7. customthe solvent was evaporated away
  8. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

Sources & evidence

ORD record
ord-52213c1b74744ea484d2797ba2e99779
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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