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

HRID 17587ノート

反応式

HRID 17587 の反応式
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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-52213c1b74744ea484d2797ba2e99779
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

読み込み中…