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

HRID 1912464ノート

反応式

HRID 1912464 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11026Titanium isopropoxide触媒HCID 1140Toluene溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-eb00270fae33410fa5888d2354612190
出典データセット
uspto-grants-2013_12
特許番号
US08609660B2

反応ノート

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