Acetic Acid → 5-(4-Bromophenyl)-2-methoxy-5,6,6-trimethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

HRID 339887Notes

Reaction equation

HRID 339887 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([S:14]([NH2:17])(=[O:16])=[O:15])([C:10]([OH:13])([CH3:12])[CH3:11])[CH3:9])=[CH:4][CH:3]=1.C(O)(=O)C.[CH3:22][O:23][C:24](OC)(OC)OC>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH3:9])[C:10]([CH3:11])([CH3:12])[O:13][C:22]([O:23][CH3:24])=[N:17][S:14]2(=[O:15])=[O:16])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 74613Tetramethyl orthocarbonateHCID 682917312-(4-Bromophenyl)-3-hydroxy-3-methylbutane-2-sulfonamide

Product 1

HCID 683592305-(4-Bromophenyl)-2-methoxy-5,6,6-trimethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

Conditions

Temperature
100 °C

Procedure

A suspension of 2.01 g of 2-(4-bromophenyl)-3-hydroxy-3-methylbutane-2-sulfonamide in 15 ml of tetramethoxymethane was admixed with 3 ml of acetic acid and stirred at 100° C. for 1.5 hours. After the removal of the solvent under reduced pressure, the crude product was purified by means of normal phase chromatography using a Flashmaster with an n-heptane/ethyl acetate gradient. The product-containing fractions were combined, concentrated by rotary evaporation and dried under high vacuum. This gave the product (0.21 g) with a molecular weight of 362.2 g/mol (C13H16BrNO4S).

Workup

  1. customAfter the removal of the solvent under reduced pressure
  2. customthe crude product was purified by means of normal phase chromatography
  3. concentrationconcentrated by rotary evaporation
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-1101f9922c7a4a5f81fb04b78e93ea53
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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