Chloroacetonitrile → (3,4-Dimethoxy-phenylsulfanyl)-acetonitrile

HRID 458796

반응식

HRID 458796 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl[CH2:13][C:14]#[N:15].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][CH2:13][C:14]#[N:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

참가 물질

7

반응물 4

HCID 7856ChloroacetonitrileHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1365393,4-Dimethoxybenzene-1-thiol

생성물 1

HCID 12698215(3,4-Dimethoxy-phenylsulfanyl)-acetonitrile수율 84%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of 3,4-dimethoxythiophenol (5.0 g, 29.4 mmol) in dry DMF (150 ml), were added chloroacetonitrile (1.85 ml, 29.4 mmol), anhydrous K2CO3 (6.09 g, 44.1 mmol) and DMAP (358 mg, 2.9 mmol). The reaction mixture was stirred at 80° C. for 20 h under nitrogen. After cooling, the mixture was filtered and concentrated in vacuo. The residue was combined with H2O, extracted with CH2Cl2, the combined organic phases were dried over anhydrous MgSO4, filtered and concentrated to give a crude oil. Flash chromatography (AcOEt) gave the title product (5.16 g, 84%).

후처리

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated in vacuo
  4. extractionextracted with CH2Cl2
  5. dry with materialthe combined organic phases were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude oil

출처 및 근거

ORD 기록
ord-0035c8957c2f4741b38e3f5d494f953c
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192950B2

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