1,2-Dichlorobenzene → 3-(2-chlorophenyl)-5-(2-fluoro-5-hexylphenyl) 1-methyl-1H-1,2,4-triazole

HRID 1940707ノート

反応式

HRID 1940707 の反応式
[CH3:1][N:2](S(C1C=CC=CC=1)(=O)=O)[N:3]=[C:4](Cl)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11].[F:22][C:23]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:27][C:24]=1[C:25]#[N:26].[Cl-].[Al+3].[Cl-].[Cl-].ClC1C=CC=CC=1Cl>C(Cl)(Cl)Cl>[Cl:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:4]1[N:26]=[C:25]([C:24]2[CH:27]=[C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:29]=[CH:30][C:23]=2[F:22])[N:2]([CH3:1])[N:3]=1

参加物

6

反応物 4

HCID 72391,2-DichlorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 214636622-Fluoro-5-hexylbenzonitrileHCID 54508988N-methyl-N-phenylsulfonyl-2-chlorobenzohydrazonoyl chloride

生成物 1

HCID 214636793-(2-chlorophenyl)-5-(2-fluoro-5-hexylphenyl) 1-methyl-1H-1,2,4-triazole収率 71.8%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
140 °C

実験手順

A mixture of N-methyl-N-(benzenesulfonyl)-2-chlorobenzohydrazonoyl chloride (2.06 g), 2-fluoro-5-hexylbenzonitrile (1.23 g), anhydrous aluminum chloride (0.88 g) and o-dichlorobenzene (5 ml) is stirred at an oil bath temperature of 140° C. for 30 minutes. After cooling, the reaction mixture is dissolved in chloroform (200 ml), washed with dilute hydrochloric acid, dilute aqueous solution of sodium hydroxide and saline in this order, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate is purified by silica gel column chromatography using mixed solvent of hexane-ethyl acetate as eluent to give 1.60 g of desired compound (refractive index: 1.5779).

後処理

  1. temperatureAfter cooling
  2. washwashed with dilute hydrochloric acid, dilute aqueous solution of sodium hydroxide and saline in this order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate is purified by silica gel column chromatography
  6. additionusing mixed solvent of hexane-ethyl acetate as eluent

出典と根拠

ORDレコード
ord-a623d881903e48f5afb9694dca1323f2
出典データセット
uspto-grants-1997_12
特許番号
US05700824

反応ノート

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