4-Chlorobenzonitrile → HCID 178503254、化合物

HRID 901894

反応式

HRID 901894 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.[CH3:14][S:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1>>[Cl:5][C:6]1[CH:13]=[CH:12][C:9]([C:10](=[NH:11])[NH:20][C:19]2[CH:21]=[CH:22][C:16]([S:15][CH3:14])=[CH:17][CH:18]=2)=[CH:8][CH:7]=1

参加物

4

反応物 3

HCID 121634-ChlorobenzonitrileHCID 660384-(Methylthio)anilineHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 178503254HCID 178503254、化合物収率 43.4%

反応条件

温度
185 °C

実験手順

Finely powdered anhydrous aluminium chloride (0.83 g, 6 mmol) was added to a stirred mixture of 4-chlorobenzonitrile (0.6875 g, 5 mmol) and 4-methylthioaniline (0.695 g, 5 mmol) over a period of 30 min. The reaction mixture was heated at 180-190° C. for 3 hours with stirring and allowed to cool to 50° C. The resultant mixture was triturated with ethyl acetate and basified with sodium hydroxide (20%) solution. The ethyl acetate layer was washed with water, dried over anhydrous sodium sulphate and concentrated to give the crude product, which was purified by column chromatography to yield the title compound (0.6 g, 43.4%, purity 98.8% by HPLC), mp 148-150° C. 1H-NMR (CDCl3):δ 2.48 (s, 3H), 6.90-6.97(m, 2H), 7.11-7.41(m, 4H), 7.74 (bs, 2H). MS m/z:277.0 (M+)

後処理

  1. temperatureto cool to 50° C
  2. customThe resultant mixture was triturated with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customto give the crude product, which
  7. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-b811785ca7544ad4885101366af2fe23
出典データセット
uspto-grants-2008_04
特許番号
US07365069B2

関連ノート

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