Hydrochloric Acid → (2-Amino-5-chlorophenyl)(2,5-dichlorophenyl)methanone

HRID 747607

反応式

HRID 747607 の反応式
ClB(Cl)Cl.[Cl:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1.[Cl:13][C:14]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:15]=1[C:16]#N.[Cl-].[Cl-].[Cl-].[Ga+3].Cl.C(OCC)(=[O:30])C>ClCCCl>[NH2:10][C:9]1[CH:11]=[CH:12][C:6]([Cl:5])=[CH:7][C:8]=1[C:16]([C:15]1[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:14]=1[Cl:13])=[O:30]

参加物

8

反応物 6

HCID 313Hydrochloric AcidHCID 78124-ChloroanilineHCID 8857Ethyl AcetateHCID 25135Boron TrichlorideHCID 890002,5-DichlorobenzonitrileHCID 186022Gallium monochloride

生成物 1

HCID 64422569(2-Amino-5-chlorophenyl)(2,5-dichlorophenyl)methanone

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
80 °C

実験手順

To 28 ml of a 1M solution of trichloroborane at −5° C. are added 5.6 g of 4-chloroaniline dissolved in 30 ml of 1,2-dichloroethane. After 45 minutes at +15° C., 3.8 g of 2,5-dichlorobenzonitrile and 5 g of gallium trichloride are introduced and the mixture is refluxed for 3 hours. At room temperature, the resulting mixture is hydrolysed with 2M hydrochloric acid solution and maintained at 80° C. for 2 hours. The reaction medium is taken up in ethyl acetate and washed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica gel, eluting with a cyclohexane/dichloromethane gradient to give 6.38 g of the expected product.

後処理

  1. temperaturethe mixture is refluxed for 3 hours
  2. customAt room temperature
  3. washwashed with water
  4. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is chromatographed on a column of silica gel
  7. washeluting with a cyclohexane/dichloromethane gradient

出典と根拠

ORDレコード
ord-3778420d222746b59b371cebcda9fedb
出典データセット
uspto-grants-2008_07
特許番号
US07396958B2

関連ノート

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