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

HRID 458796

反応式

HRID 458796 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-0035c8957c2f4741b38e3f5d494f953c
出典データセット
uspto-grants-2007_03
特許番号
US07192950B2

関連ノート

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