Sodium Cyanide → Benzo[b]thiophene-3-acetonitrile

HRID 501208

반응식

HRID 501208 반응식
[C-:1]#[N:2].[Na+].Cl[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:8][CH:7]=1>CS(C)=O>[S:8]1[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:6]([CH2:5][C:1]#[N:2])=[CH:7]1

참가 물질

4

반응물 2

HCID 8929Sodium CyanideHCID 766803-(Chloromethyl)benzo(b)thiophene

생성물 1

HCID 76681Benzo[b]thiophene-3-acetonitrile수율 65.9%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

To a stirred solution of NaCN (1.4 g, 28.5 mmol) in DMSO (8 mL) was added 3-(chloromethyl)-1-benzothiophene (4 gm, 21.9 mmol) in DMSO (6 mL) over 15 min. The reaction mixture was stirred at room temperature for 18 h and then quenched with water and extracted with ether (2×50 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography using ethyl acetate-hexane (1:1) to furnish 1-benzothien-3-ylacetonitrile (2.5 g, 65%). 1H NMR (200 MHz, CDCl3): δ 3.69 (s, 2H), 7.25-7.91 (m, 5H).

후처리

  1. customquenched with water
  2. extractionextracted with ether (2×50 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-9e9a173a102d4360b87ed539b30a777f
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772245B2

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