Water → 2-(3-(2,6-Difluorophenyl)pyrazol-1-yl)-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrile

HRID 1822628노트

반응식

HRID 1822628 반응식
[C:1]([CH2:3][N:4]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=2[F:16])=[N:5]1)#[N:2].[H-].[Na+].[CH3:19][N:20]1[C:24]([Cl:25])=[C:23]([C:26](N2C=CC=N2)=[O:27])[C:22]([Cl:33])=[N:21]1.O>C1COCC1>[F:15][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([F:16])[C:9]=1[C:6]1[CH:7]=[CH:8][N:4]([C:3](=[C:26]([C:23]2[C:22]([Cl:33])=[N:21][N:20]([CH3:19])[C:24]=2[Cl:25])[OH:27])[C:1]#[N:2])[N:5]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 221694981-Cyanomethyl-3-(2,6-difluorophenyl)pyrazoleHCID 221695221-(1-Methyl-3,5-dichloropyrazole-4-carbonyl)pyrazole

생성물 1

HCID 573044512-(3-(2,6-Difluorophenyl)pyrazol-1-yl)-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrile수율 57.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

A solution of 0.5 g of 1-cyanomethyl-3-(2,6-difluorophenyl)pyrazole dissolved in 10 ml of THF was dropwise added to a suspension of 0.15 g of 55% sodium hydride in 10 ml of THF, at 50° C. After the resulting product was stirred for 30 minutes, a solution of 0.67 g of 1-(1-methyl-3,5-dichloropyrazole-4-carbonyl)pyrazole dissolved in 10 ml of THF was dropwise added thereto at 50° C. and then stirred overnight at room temperature. The reaction mixture was poured into water, then extracted with ethyl acetate and washed with a small amount of water. The resulting product was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was recrystallized from a mixed solvent of isopropyl ether/ethyl acetate=3/1 to obtain 0.52 g of 2-{3-(2,6-difluorophenyl)pyrazol-1-yl}-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrile.

후처리

  1. additionwas dropwise added
  2. stirringat 50° C. and then stirred overnight at room temperature
  3. extractionextracted with ethyl acetate
  4. washwashed with a small amount of water
  5. dry with materialThe resulting product was dried over sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residual product was recrystallized from a mixed solvent of isopropyl ether/ethyl acetate=3/1

출처 및 근거

ORD 기록
ord-033e5827392c441386ba3d602c731d77
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07037880B2

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