4-(Trifluoromethyl)benzenesulfonamide → N-((3-iodo-1-(methoxymethyl)-1H-pyrazol-4-yl)methylene)-4-(trifluoromethyl)benzenesulfonamide

HRID 1011616

반응식

HRID 1011616 반응식
[I:1][C:2]1[C:6]([CH:7]=O)=[CH:5][N:4]([CH2:9][O:10][CH3:11])[N:3]=1.[F:12][C:13]([F:25])([F:24])[C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1>C1COCC1.[Cl-].[Na+].O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[I:1][C:2]1[C:6]([CH:7]=[N:23][S:20]([C:17]2[CH:16]=[CH:15][C:14]([C:13]([F:12])([F:25])[F:24])=[CH:19][CH:18]=2)(=[O:21])=[O:22])=[CH:5][N:4]([CH2:9][O:10][CH3:11])[N:3]=1

참가 물질

6

반응물 2

HCID 700184-(Trifluoromethyl)benzenesulfonamideHCID 576597643-Iodo-1-(methoxymethyl)-1H-pyrazole-4-carbaldehyde

생성물 1

HCID 67313312N-((3-iodo-1-(methoxymethyl)-1H-pyrazol-4-yl)methylene)-4-(trifluoromethyl)benzenesulfonamide

시약·촉매·용매 3

HCID 76524Titanium tetraethoxide촉매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

3-Iodo-1-(methoxymethyl)-1H-pyrazole-4-carbaldehyde (39) (2.0 g, 7.52 mmol) and 4-(trifluoromethyl)benzenesulfonamide (40) (1.69 g, 7.52 mmol) were dissolved in THF (20 mL) under nitrogen. Titanium(IV) ethoxide (7.8 mL, 37.6 mmol) was added via syringe and the reaction stirred for 16 hr at rt. The reaction was poured into brine (50 mL) and filtered through a pad of Celite. The filtrate was extracted with EtOAc (3×50 mL) and the combined organics were washed with brine (100 mL), dried over Na2SO4, and concentrated in vacuo to give N-((3-iodo-1-(methoxymethyl)-1H-pyrazol-4-yl)methylene)-4-(trifluoromethyl)benzenesulfonamide (41) as a clear oil that was used without further purification.

후처리

  1. filtrationfiltered through a pad of Celite
  2. extractionThe filtrate was extracted with EtOAc (3×50 mL)
  3. washthe combined organics were washed with brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-18b12a13eaee4612ab3c910786c31e50
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977368B2

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