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

HRID 52235노트

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HRID 52235 반응식
[CH3:1][N:2](S(C1C=CC=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[F:12].[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][N:34]=1)[C:27]#[N:28].ClC1C=CC=CC=1Cl>C(Cl)(Cl)Cl.[Fe](Cl)(Cl)Cl>[Cl:23][C:24]1[CH:25]=[C:26]([C:27]2[N:2]([CH3:1])[N:3]=[C:4]([C:5]3[C:6]([F:12])=[CH:7][CH:8]=[CH:9][C:10]=3[F:11])[N:28]=2)[CH:29]=[CH:30][C:31]=1[O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]([F:40])([F:41])[F:42])=[CH:35][N:34]=1

참가 물질

6

반응물 3

HCID 72391,2-DichlorobenzeneHCID 214636733-Chloro-4-(5-trifluoromethylpyridine-2-yloxy)benzonitrileHCID 53707170N-methyl-N-(benzenesulfonyl)-2,6-difluorobenzohydrazonoyl chloride

생성물 1

HCID 214636745-[3-chloro-4-(5-trifluoromethylpyridine-2-yloxy)phenyl]-3-(2,6-difluorophenyl)-1-methyl-1H-1,2,4-triazole수율 53.7%

시약·촉매·용매 2

HCID 24380Iron chloride (FeCl3)촉매HCID 6212Chloroform용매

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온도
140 °C

실험 절차

A mixture of N-methyl-N-(benzenesulfonyl)-2,6-difluorobenzohydrazonoyl chloride (1.72 g), 3-chloro-4-(5-trifluoromethylpyridine-2-yloxy)benzonitrile (1.50 g), anhydrous iron (III) chloride (0.85 g) and o-dichlorobenzene (10 ml) is stirred at an oil bath temperature of 140° C. for 30 minutes. After cooling, it is dissolved in chloroform (200 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 and washed with hexane to give 1.25 g of desired compound.

후처리

  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
  7. washwashed with hexane

출처 및 근거

ORD 기록
ord-c767ede186ba4f4fb588a224557f7e00
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616594

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