Sulfur Dioxide → N-(1,1-Dimethylethyl)-1-[tris(1-methylethyl)silyl]-1H-pyrrole-3-sulfonamide

HRID 1707928

反応式

HRID 1707928 の反応式
Br[C:2]1[CH:6]=[CH:5][N:4]([Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])[CH:3]=1.C([Li])CCC.[S:22](=[O:24])=[O:23].ClN1C(=O)CCC1=O.[C:33]([NH2:37])([CH3:36])([CH3:35])[CH3:34]>O1CCCC1>[CH3:34][C:33]([NH:37][S:22]([C:2]1[CH:6]=[CH:5][N:4]([Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])[CH:3]=1)(=[O:24])=[O:23])([CH3:36])[CH3:35]

参加物

7

反応物 5

HCID 1119Sulfur DioxideHCID 6385Tert-ButylamineHCID 31398ChlorosuccinimideHCID 27633023-Bromo-1-(triisopropylsilyl)pyrroleHCID 178418339Butyllithium

生成物 1

HCID 18960403N-(1,1-Dimethylethyl)-1-[tris(1-methylethyl)silyl]-1H-pyrrole-3-sulfonamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 4.55 g (0.0151 mol) of 3-bromo-N-triisopropylsilylpyrrole in 100 mL anhydrous tetrahydrofuran (THF) under nitrogen atmosphere was cooled to -60° C. then treated with 10.4 mL of 1.6M butyllithium in hexanes (0.0166 mol) dropwise at such a rate as to keep the temperature below -60° C. After ca. 30 minutes at this temperature, liquified sulfur dioxide was added (3.9 mL, 0.090 mol). The brown solution was then warmed to room temperature, and the THF was removed under reduced pressure. The resulting light brown solid was dissolved in 100 mL acetic acid and then treated with 2.0 g (0.015 mol) N-chlorosuccinimide with cooling to keep the temperature less than 25° C. After 2 hours, the acetic acid was evaporated under reduced pressure and the residue taken up in ethyl acetate. This solution was washed successively with water, NaHCO3 solution, 5% NaHSO3 solution, NaHCO3 solution, brine, then dried with MgSO4 and evaporated in vacuo. The resulting dark brown oil residue was dissolved in methylene chloride (200 mL) and treated with 8 mL (0.075 mol) t-butylamine and then stirred for 3 days at ambient temperature. The solution was then washed with 1N HCl, dried (MgSO4), and evaporated to a dark oil. Chromatography on silica gel (10% ethyl acetate/hexanes) afforded 4.0 g of the title compound as an amber oil that solidified on standing.

後処理

  1. customthe temperature below -60° C
  2. customthe THF was removed under reduced pressure
  3. dissolutionThe resulting light brown solid was dissolved in 100 mL acetic acid
  4. temperaturewith cooling
  5. customthe temperature less than 25° C
  6. customthe acetic acid was evaporated under reduced pressure
  7. washThis solution was washed successively with water, NaHCO3 solution, 5% NaHSO3 solution, NaHCO3 solution, brine
  8. dry with materialdried with MgSO4
  9. customevaporated in vacuo
  10. dissolutionThe resulting dark brown oil residue was dissolved in methylene chloride (200 mL)
  11. washThe solution was then washed with 1N HCl
  12. dry with materialdried (MgSO4)
  13. customevaporated to a dark oil

出典と根拠

ORDレコード
ord-d5014261c16d42b6805e210cbda399b5
出典データセット
uspto-grants-1994_10
特許番号
US05356862

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