Sulfur Dioxide → 3-(2,5,5-Trimethyl-1,3-dioxan-2-yl)thiophene-2-sulfonamide

HRID 1735986노트

반응식

HRID 1735986 반응식
[CH3:1][C:2]1([C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[O:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH2:4][O:3]1.C([Li])CCC.[S:20](=[O:22])=[O:21].O.O.O.C([O-])(=O)C.[Na+].[NH2:31]OS(O)(=O)=O>CCCCCC.O.C1COCC1>[CH3:1][C:2]1([C:10]2[CH:14]=[CH:13][S:12][C:11]=2[S:20]([NH2:31])(=[O:22])=[O:21])[O:3][CH2:4][C:5]([CH3:8])([CH3:9])[CH2:6][O:7]1

참가 물질

10

반응물 5

HCID 1119Sulfur DioxideHCID 76284hydroxylamine-O-sulfonic acidHCID 22902024HCID 22902024, 화합물HCID 23665404Sodium Acetate TrihydrateHCID 178418339Butyllithium

생성물 1

HCID 229019383-(2,5,5-Trimethyl-1,3-dioxan-2-yl)thiophene-2-sulfonamide

시약·촉매·용매 4

HCID 8058Hexane촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

To a solution of 3-(2,5,5-trimethyl-1,3-dioxan-2-yl)thiophene (106 g, 0.5 mol) in hexane (1200 mL) at -60° C. was added a 2.5M solution of n-butyllithium in hexane (240 mL, 0.6 mmol) over 40 min. The mixture was allowed to warm to room temperature (approximately 1.5 hr) and then once again cooled to -60° C. and anhydrous THF (400 mL) added. Sulfur dioxide was passed over the surface of the reaction mixture for 30 min at which point the reaction mixture was allowed to warm to room temperature under a positive SO2 pressure (approximately 1 hr). The solvent was removed and the residue dissolved in water (1200 mL) to which sodium acetate trihydrate (217.73 g, 1.6 mol) was added. The solution was cooled (ice bath) to 0° C. and hydroxylamine-O-sulfonic acid (107 g, 0.95 mol) was slowly added. The mixture was stirred at room temperature for 18 hr and then extracted with ethyl acetate. The combined extracts were washed with a saturated aqueous sodium bicarbonate solution, brine, dried (Na2SO4) and evaporated to give a viscous brown oil (174.05 g); this product was used in the next step without further purification.

후처리

  1. temperatureonce again cooled to -60° C.
  2. temperatureto warm to room temperature under a positive SO2 pressure (approximately 1 hr)
  3. customThe solvent was removed
  4. additionwas added
  5. temperatureThe solution was cooled (ice bath) to 0° C.
  6. extractionextracted with ethyl acetate
  7. washThe combined extracts were washed with a saturated aqueous sodium bicarbonate solution, brine
  8. dry with materialdried (Na2SO4)
  9. customevaporated

출처 및 근거

ORD 기록
ord-987f0326a8544d36a1cc6fd9e8d729d2
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05538966

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