Acetic Acid → 1,2,4,5-Tetrahydrobenzo[d][1,2]thiazepine 3,3-dioxide

HRID 1743123Notes

Reaction equation

HRID 1743123 reaction equation
[C:1]1([CH2:7][CH2:8][S:9]([NH2:12])(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13](O)(=O)C.O1CCCOO1.O>CS(O)(=O)=O.FC(F)(F)C(O)=O>[CH2:13]1[C:6]2[CH:5]=[CH:4][CH:3]=[CH:2][C:1]=2[CH2:7][CH2:8][S:9](=[O:10])(=[O:11])[NH:12]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 204808BenzeneethanesulfonamideHCID 19593658CID 19593658

Product 1

HCID 130116511,2,4,5-Tetrahydrobenzo[d][1,2]thiazepine 3,3-dioxide

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of 2-phenylethanesulfonamide (3.62 g) in methanesulfonic acid (20 ml)-acetic acid (5 ml) was added a solution of trioxane (582 mg) in trifluoroacetic acid (3 ml) and the mixture was stirred for 3 hours at 35° C. To the reaction mixture was added water and was extracted with chloroform. The organic layer was washed with water and a saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate and was concentrated. The residue was purified by column chromatography on silica gel (chloroform:methanol=100:1) to give the title compound (1.78 g) having the following physical data.

Workup

  1. extractionwas extracted with chloroform
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate
  4. concentrationwas concentrated
  5. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-a6f14f7285984316a80476b0a9f059d7
Source dataset
uspto-grants-2006_03
Patent number
US07008938B2

Reaction notes

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