Sodium Cyanide → 3-(5-Bromobenzo[b]thien-2-yl)-2-(4-methoxyphenyl)butyronitrile

HRID 361914

반응식

HRID 361914 반응식
[C-:1]#[N:2].[Na+].CS(OC[CH:10]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[CH2:11][C:12]1[S:16][C:15]2[CH:17]=[CH:18][C:19]([Br:21])=[CH:20][C:14]=2[CH:13]=1)(=O)=O.[C:30](OCC)(=O)C.C1(C)C=CC=CC=1>CS(C)=O>[Br:21][C:19]1[CH:18]=[CH:17][C:15]2[S:16][C:12]([CH:11]([CH3:30])[CH:10]([C:22]3[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=3)[C:1]#[N:2])=[CH:13][C:14]=2[CH:20]=1

참가 물질

5

반응물 3

HCID 8929Sodium CyanideHCID 21584019Toluene ethylacetateHCID 218443143-(5-Bromobenzo[b]thien-2-yl)-2-(4-methoxyphenyl)propyl methanesulfonate

생성물 1

HCID 218443933-(5-Bromobenzo[b]thien-2-yl)-2-(4-methoxyphenyl)butyronitrile

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
80 °C

실험 절차

1H-NMR (CDCl3) δ: 3.78 (3H, s), 3.9-4.5 (3H, m), 3.70 (3H, s), 4.3 (2H, m), 6.70-7.80 (8H, m) e) 1.2 g of sodium cyanide was dissolved in 30 ml of dimethyl sulfoxide at a temperature of 90° C. To this was gradually added 18.5 g of 3-(5-bromobenzo[b]thien-2-yl)-2-(4-methoxyphenyl)propyl methanesulfonate, followed by stirring at 80° C. for 1 hour. The resulting reaction solution was mixed with an ethyl acetate/toluene mixture, washed with water, and then dried to distill off the solvent. Crystals thus precipitated were washed with ethanol and dried to obtain 5 g of 3-(5-bromobenzo[b]thien-2-yl)-2-(4-methoxyphenyl)butyronitrile. The same compound was also obtained with a yield of 2 g, by concentrating the ethanol solution resulting from the washing of crystals and subjecting the concentrate to silica gel column chromatography using chloroform as an elution solvent.

후처리

  1. customThe resulting reaction solution
  2. washwashed with water
  3. customdried
  4. distillationto distill off the solvent
  5. customCrystals thus precipitated
  6. washwere washed with ethanol
  7. customdried

출처 및 근거

ORD 기록
ord-bd1a795f7ef64356a9bd7fe7a039aee8
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866577

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