Pyridine → alpha-Cypermethrin 1-Epimeric Mixture

HRID 443769

반응식

HRID 443769 반응식
[C:1]([CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=1)[OH:4])#[N:2].[Cl:18][C:19]([Cl:29])=[CH:20][C@@H:21]1[C@H:23]([C:24](Cl)=[O:25])[C:22]1([CH3:28])[CH3:27].N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:18][C:19]([Cl:29])=[CH:20][C@@H:21]1[C@H:23]([C:24]([O:4][CH:3]([C:1]#[N:2])[C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:6]=2)=[O:25])[C:22]1([CH3:27])[CH3:28]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 93218Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-HCID 12617358cis-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropylcarbonyl chloride

생성물 1

HCID 9801977alpha-Cypermethrin 1-Epimeric Mixture수율 106.1%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
40 °C

실험 절차

A mixture of 468.6 g (2.08 moles) (cyano)(3-phenoxyphenyl)methanol and 2500 ml toluene was placed in a flask and heated to 40° C. During an 80-85 minute period, 509 g (2.24 moles) of (cis)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarbonyl chloride prepared as described in Step B, and 186 g (2.35 moles) of pyridine were added under nitrogen. Upon completion of the addition, the reaction mixture was stirred 2.5 hours at 40° C. After cooling, the reaction mixture was washed successively with 1000 ml of water, 1000 ml of 1 N hydrochloric acid, 1000 ml of 1 N sodium hydroxide, twice with water, and once with an aqueous solution of sodium chloride. After being dried over magnesium sulfate, the solution was filtered through Celite and the solvent stripped using a rotary evaporator. Residual solvent was removed in a vacuum oven. A total of 918.3 g of 93.6% (cyano)(3-phenoxyphenyl)methyl cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate was obtained.

후처리

  1. customwas placed in a flask
  2. additionwere added under nitrogen
  3. additionUpon completion of the addition
  4. temperatureAfter cooling
  5. washthe reaction mixture was washed successively with 1000 ml of water, 1000 ml of 1 N hydrochloric acid, 1000 ml of 1 N sodium hydroxide, twice with water
  6. dry with materialAfter being dried over magnesium sulfate
  7. filtrationthe solution was filtered through Celite
  8. customa rotary evaporator
  9. customResidual solvent was removed in a vacuum oven

출처 및 근거

ORD 기록
ord-061a2ddc4e12463081fb09ea331d2d71
출처 데이터셋
uspto-grants-1981_04
특허 번호
US04261921

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