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

HRID 339869Notes

Reaction equation

HRID 339869 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([S:14]([NH2:17])(=[O:16])=[O:15])([C:10]([OH:13])([CH3:12])[CH3:11])[CH3:9])[CH:5]=[CH:6][CH:7]=1.C(O)(=O)C.[CH3:22][O:23][C:24](OC)(OC)OC>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:9])[C:10]([CH3:12])([CH3:11])[O:13][C:22]([O:23][CH3:24])=[N:17][S:14]2(=[O:15])=[O:16])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 74613Tetramethyl orthocarbonateHCID 682923112-(3-Bromophenyl)-3-hydroxy-3-methylbutane-2-sulfonamide

Product 1

HCID 683591715-(3-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 1.10 g of 2-(3-bromophenyl)-3-hydroxy-3-methylbutane-2-sulfonamide in 10 ml of tetramethoxymethane was admixed with 2 ml of acetic acid and stirred at 100° C. for 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 and concentrated by rotary evaporation. This gave the product (0.61 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

Sources & evidence

ORD record
ord-0d0210f4729a4b8b839554205c90af4d
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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