Water → 2-(4-Chlorophenyl)-2-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]oxirane

HRID 2371911노트

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HRID 2371911 반응식
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[Cl:9][C:10]1[CH:26]=[CH:25][C:13]([C:14]([C:16]2([N:19]3[CH:23]=[N:22][C:21]([Cl:24])=[N:20]3)[CH2:18][CH2:17]2)=[O:15])=[CH:12][CH:11]=1.O>CS(C)=O>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]2([C:16]3([N:19]4[CH:23]=[N:22][C:21]([Cl:24])=[N:20]4)[CH2:17][CH2:18]3)[CH2:4][O:15]2)=[CH:25][CH:26]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 146972271-(4-Chlorobenzoyl)-1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropane

생성물 1

HCID 146972292-(4-Chlorophenyl)-2-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]oxirane수율 100%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

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온도
40 °C

실험 절차

60 ml of absolute dimethyl sulphoxide are added dropwise at 10° C. under a nitrogen atmosphere to a stirred mixture of 2.5 g (83 mmol) of sodium hydride (80 per cent of substance) and 17.6 g (80 mmol) of trimethyl sulphoxonium iodide. Stirring is continued for one hour at 20° C., and a solution of 20 g (71 mmol) of 1-(4-chlorobenzoyl)-1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropane in 30 ml of dimethyl sulphoxide is subsequently added at 10° C. After the reaction mixture has been stirred for 48 hours at 20° C., it is warmed for another hour at 40° C. and then poured into water. The mixture is extracted several times using ethyl acetate, and the combined organic phases are washed with water, dried over sodium sulphate and concentrated by stripping off the solvent under reduced pressure. This procedure gives 21 g (100% of theory) of 2-(4-chlorophenyl)-2-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]-oxirane in the form of an oil. 1H-NMR (200 MHz, CDCl3): δ=0.8-1.4 (m, 4H); 2.92 (d, 1H); 3.15 (d, 1H); 7.10 (d, 2 H); 7.38 (d, 2H); 7.75 (s, 1H). ##STR18##

후처리

  1. stirringAfter the reaction mixture has been stirred for 48 hours at 20° C.
  2. extractionThe mixture is extracted several times
  3. washthe combined organic phases are washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-67a00124b04449b1abe2050bff1c5783
출처 데이터셋
uspto-grants-1992_03
특허 번호
US05096913

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