1,2-Dichlorobenzene → 3-(2-chloro-6-fluorophenyl)-5-(2-chloro-4-nitrophenyl) 1-methyl-1H-1,2,4-triazole

HRID 52206

反応式

HRID 52206 の反応式
[CH3:1][N:2](S(C1C=CC(C)=CC=1)(=O)=O)[N:3]=[C:4](Cl)[C:5]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:12].[Cl:24][C:25]1[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][C:26]=1[C:27]#[N:28].ClC1C=CC=CC=1Cl>C(Cl)(Cl)Cl.[Fe](Cl)(Cl)Cl>[Cl:12][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([F:11])[C:5]=1[C:4]1[N:28]=[C:27]([C:26]2[CH:29]=[CH:30][C:31]([N+:33]([O-:35])=[O:34])=[CH:32][C:25]=2[Cl:24])[N:2]([CH3:1])[N:3]=1

参加物

6

反応物 3

HCID 72391,2-DichlorobenzeneHCID 1414012-Chloro-4-nitrobenzonitrileHCID 54347086N-methyl-N-(p-toluenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride

生成物 1

HCID 214636043-(2-chloro-6-fluorophenyl)-5-(2-chloro-4-nitrophenyl) 1-methyl-1H-1,2,4-triazole収率 118.3%

試薬・触媒・溶媒 2

HCID 24380Iron chloride (FeCl3)触媒HCID 6212Chloroform溶媒

反応条件

温度
140 °C

実験手順

A mixture of N-methyl-N-(p-toluenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride (1.90 g), 2-chloro-4-nitrobenzonitrile (1.80 g), anhydrous iron (III) chloride (1.60 g) and o-dichlorobenzene (5 ml) is stirred at an oil bath temperature of 140° C. for 1 hour. After cooling, the reaction mixture is dissolved in chloroform (100 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 2.20 g of desired compound (melting point: 144.0°-148.0° C.).

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-d9ee018728f746e7a5dd5c3746938ef1
出典データセット
uspto-grants-1997_04
特許番号
US05616594

関連ノート

読み込み中…