4-Chlorobenzonitrile → HCID 178503254, compound

HRID 901894

Reaction equation

HRID 901894 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

HCID 178503254HCID 178503254, compoundYield 43.4%

Conditions

Temperature
185 °C

Procedure

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+)

Workup

  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

Sources & evidence

ORD record
ord-b811785ca7544ad4885101366af2fe23
Source dataset
uspto-grants-2008_04
Patent number
US07365069B2

Linked notes

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