4-Chlorobenzonitrile → HCID 178503254, 화합물

HRID 901894

반응식

HRID 901894 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

HCID 178503254HCID 178503254, 화합물수율 43.4%

반응 조건

온도
185 °C

실험 절차

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+)

후처리

  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

출처 및 근거

ORD 기록
ord-b811785ca7544ad4885101366af2fe23
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365069B2

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