Sulfuric Acid → HCID 23363812, compound

HRID 1081281Notes

Reaction equation

HRID 1081281 reaction equation
[OH:1][CH:2]1[C:7]2[CH:8]=[C:9]([S:11]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])=[O:12])[S:10][C:6]=2[S:5](=[O:20])(=[O:19])[NH:4][CH2:3]1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.OS(O)(=O)=O>CC(C)=O.O>[CH3:18][C:15]([NH:14][S:11]([C:9]1[S:10][C:6]2[S:5](=[O:20])(=[O:19])[NH:4][CH2:3][C:2](=[O:1])[C:7]=2[CH:8]=1)(=[O:13])=[O:12])([CH3:16])[CH3:17]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 22901902HCID 22901902, compoundHCID 131709961Jones' reagent

Product 1

HCID 23363812HCID 23363812, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 3,4-dihydro-4-hydroxy-N-(1,1-dimethylethyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide (3.36 g, 9.87 mmol) in acetone (15 mL) at room temperature was added Jones reagent [2 mL (prepared by dissolving CrO3 (7 g) in H2O (50 mL) and adding H2SO4 (6.1 mL)]. The mixture was stirred at room temperature for one hour, solvent was evaporated and the residue dissolved in ethyl acetate (75 mL). This solution was washed with saturated aqueous sodium bicarbonate until the the organic layer was neutral. The aqueous layer was separated and washed with ethyl acetate (3'25 mL). The combined extracts were dried (NaSO4) and evaporated to provide a residue which was purified by column chromatography (silica, 40% ethyl acetate in hexane) to give an off-white solid (2.74 g, 82%): mp 170°-172° C.

Workup

  1. customprepared
  2. customsolvent was evaporated
  3. dissolutionthe residue dissolved in ethyl acetate (75 mL)
  4. washThis solution was washed with saturated aqueous sodium bicarbonate until the the organic layer
  5. customThe aqueous layer was separated
  6. washwashed with ethyl acetate (3'25 mL)
  7. dry with materialThe combined extracts were dried (NaSO4)
  8. customevaporated
  9. customto provide a residue which
  10. customwas purified by column chromatography (silica, 40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ef3b18d886534da2821806a8e885961d
Source dataset
uspto-grants-1996_12
Patent number
US05585377

Reaction notes

Loading…