Water → 1-(8-Cyanooctyl)-2,4,5-triphenyl-imidazole

HRID 1376338노트

반응식

HRID 1376338 반응식
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:12]=[C:11]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[C-:33]#[N:34].[Na+].O>CS(C)=O>[C:33]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:12]=[C:11]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)#[N:34]

참가 물질

5

반응물 3

HCID 962WaterHCID 8929Sodium CyanideHCID 229164371-(8-Bromooctyl)-2,4,5-triphenylimidazole

생성물 1

HCID 229164431-(8-Cyanooctyl)-2,4,5-triphenyl-imidazole수율 31%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

반응 조건

온도
50 °C

실험 절차

1-(8-Bromooctyl)-2,4,5-triphenylimidazole (4 g) in dimethylsulphoxide (30 ml) was added dropwise to a mixture of sodium cyanide (0.5 g) in dry dimethylsulphoxide (30 ml ). The reaction mixture was stirred at 50° C. for 2 h, cooled and poured into water (400 ml). The aqueous was extracted with diethyl ether (4×100 ml ), the extracts were combined, washed with water (100 ml), dried over anhydrous magnesinm sulphate and evaporated to dryness in vacuo. Chromatography on silica gel eluted with a dichloromethane:methanol gradient and recrystallisation from ether gave 1-(8-cyanoctyl)-2,4,5-triphenylimidazole (1.1 g, 31%) as a white solid, m.p. 72°-73°. Found: C, 83.10; H, 7.21; N, 9.69%; C30H31N3 requires: C, 82.90; H, 7.19; N, 9.57%.

후처리

  1. temperaturecooled
  2. extractionThe aqueous was extracted with diethyl ether (4×100 ml )
  3. washwashed with water (100 ml)
  4. dry with materialdried over anhydrous magnesinm sulphate
  5. customevaporated to dryness in vacuo
  6. washChromatography on silica gel eluted with a dichloromethane
  7. custommethanol gradient and recrystallisation from ether

출처 및 근거

ORD 기록
ord-863adee5e719461987822920916732c8
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05663053

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