Tert-Butanesulfinamide → 3-[(3-Chloro-phenyl)-(2-methyl-propane-2-sulfinylimino)-methyl]-pyrazole-1-sulfonic acid dimethylamide

HRID 1912464노트

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HRID 1912464 반응식
[CH3:1][N:2]([CH3:20])[S:3]([N:6]1[CH:10]=[CH:9][C:8]([C:11](=O)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)=[N:7]1)(=[O:5])=[O:4].[CH3:21][C:22]([S:25]([NH2:27])=[O:26])([CH3:24])[CH3:23]>C1(C)C=CC=CC=1.[Cl-].[Na+].O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:1][N:2]([CH3:20])[S:3]([N:6]1[CH:10]=[CH:9][C:8]([C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)=[N:27][S:25]([C:22]([CH3:24])([CH3:23])[CH3:21])=[O:26])=[N:7]1)(=[O:5])=[O:4]

참가 물질

6

반응물 2

HCID 3382465Tert-ButanesulfinamideHCID 668264453-(3-chloro-benzoyl)-1H-pyrazole-1-sulfonic acid dimethylamide

생성물 1

HCID 866908083-[(3-Chloro-phenyl)-(2-methyl-propane-2-sulfinylimino)-methyl]-pyrazole-1-sulfonic acid dimethylamide수율 97.3%

시약·촉매·용매 3

HCID 11026Titanium isopropoxide촉매HCID 1140Toluene용매HCID 57417360Sodium chloride; water용매

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온도
110 °C

실험 절차

Titanium(IV)isopropoxide (3.22 mL, 10.71 mmol) was added to a mixture of 3-(3-chloro-benzoyl)-1H-pyrazole-1-sulfonic acid dimethylamide (1.68 g, 5.35 mmol) and 2-methyl-2-propanesulfinamide (0.71 g, 5.89 mmol) in toluene (32 mL) under nitrogen. The mixture was stirred at 110° C. for 24 hours. The mixture was cooled and poured into brine while rapidly stirring. The mixture was filtered through diatomaceous earth and the filter cake was washed with AcOEt. The filtrate was transferred to a separation funnel where the organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; AcOEt in DCM 0/100 to 10/90). The desired fractions were collected and concentrated in vacuo to yield 3-[(3-chloro-phenyl)-(2-methyl-propane-2-sulfinylimino)-methyl]-pyrazole-1-sulfonic acid dimethylamide (2.17 g, 97% yield) as a yellow oil.

후처리

  1. temperatureThe mixture was cooled
  2. stirringwhile rapidly stirring
  3. filtrationThe mixture was filtered through diatomaceous earth
  4. washthe filter cake was washed with AcOEt
  5. customThe filtrate was transferred to a separation funnel
  6. customwhere the organic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvents evaporated in vacuo
  10. customThe crude product was purified by flash column chromatography (silica gel; AcOEt in DCM 0/100 to 10/90)
  11. customThe desired fractions were collected
  12. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-eb00270fae33410fa5888d2354612190
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609660B2

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