1,2-Dichlorobenzene → 3-(2-chloro-6-fluorophenyl)-5-[2-chloro-4-(5-trifluoromethylpyridine-2-yloxy)phenyl]-1-methyl-1H-1,2,4-triazole

HRID 52232ノート

反応式

HRID 52232 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]([O:33][C:34]2[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][N:35]=2)[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]([O:33][C:34]3[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:41])[F:42])=[CH:36][N:35]=3)=[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 214636072-Chloro-4-(5-trifluoromethylpyridine-2-yloxy)benzonitrileHCID 54347086N-methyl-N-(p-toluenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride

生成物 1

HCID 214636873-(2-chloro-6-fluorophenyl)-5-[2-chloro-4-(5-trifluoromethylpyridine-2-yloxy)phenyl]-1-methyl-1H-1,2,4-triazole収率 53.1%

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 (2.25 g), 2-chloro-4-(5-trifluoromethylpyridine-2-yloxy)benzonitrile (1.88 g), anhydrous iron (III) chloride (1.07 g) and o-dichlorobenzene (5 ml) is stirred at an oil bath temperature of 140° C. for 30 minutes. After cooling, it is dissolved in chloroform (300 ml) and washed with dilute hydrochloric acid, dilute aqueous solution of sodium hydroxide and saline. Then, it is dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate is purified by silica gel column chromatography using mixed solvent of hexaneethyl acetate as eluent to give 1.54 g of desired compound (melting point: 139.0°-141.0° C.).

後処理

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

出典と根拠

ORDレコード
ord-3dca57f2281c4914bca04534540764e9
出典データセット
uspto-grants-1997_04
特許番号
US05616594

反応ノート

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