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

HRID 1940721
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인쇄 미리보기

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HRID 1940721 반응식
[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][CH:37]=[CH:36][CH: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][CH:37]=[CH:36][CH:35]=3)=[CH:32][C:25]=2[Cl:24])[N:2]([CH3:1])[N:3]=1
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참가 물질

6

반응물 3

HCID 72391,2-DichlorobenzeneHCID 115576702-Chloro-4-phenoxybenzonitrileHCID 54347086N-methyl-N-(p-toluenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride

생성물 1

HCID 214636213-(2-chloro-6-fluorophenyl)-5-(2-chloro-4-phenoxyphenyl) 1-methyl-1H-1,2,4-triazole수율 4.1%

시약·촉매·용매 2

HCID 24380Iron chloride (FeCl3)
촉매
HCID 6212Chloroform용매

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온도
140 °C

실험 절차

A mixture of N-methyl-N-(p-toluenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride (3.30 g), 2-chloro-4-phenoxybenzonitrile (2.30 g), anhydrous iron (III) chloride (1.60 g) and o-dichlorobenzene (10 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 hydrochrolic 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 0.15 g of desired compound (melting point: 135.0°-140.0° C.).

후처리

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

출처 및 근거

ORD 기록
ord-2689dbe3f8804cf89d1519ef62c943db
출처 데이터셋
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05700824

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