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

HRID 339891

反応式

HRID 339891 の反応式
[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.[CH2:22]([O:24][C:25](OCC)(OCC)OCC)[CH3:23]>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:9])[C:10]([CH3:12])([CH3:11])[O:13][C:25]([O:24][CH2:22][CH3:23])=[N:17][S:14]2(=[O:15])=[O:16])[CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 3

HCID 176Acetic Acid2 回HCID 66213Tetraethyl orthocarbonateHCID 682923112-(3-Bromophenyl)-3-hydroxy-3-methylbutane-2-sulfonamide

生成物 1

HCID 683592355-(3-Bromophenyl)-2-ethoxy-5,6,6-trimethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

反応条件

温度
100 °C

実験手順

A suspension of 14.40 g of 2-(3-bromophenyl)-3-hydroxy-3-methylbutane-2-sulfonamide (50%, contaminated with 1-(3-bromophenyl)ethanesulfonamide)) in 100 ml of tetraethoxymethane was admixed with 12 ml of acetic acid and stirred at 100° C. under a strong argon stream for 6 hours. After the removal of the solvent under reduced pressure (bath temperature 70° C.), the viscous residue was dried at 50° C. in a vacuum drying cabinet for 16 hours. The conversion was checked by LCMS and found to be incomplete. Therefore, the oily residue was left to react on the rotary evaporator under reduced pressure (bath temperature 80° C.) for 4 hours. After the addition of 10 ml of acetic acid, the bath temperature was increased to 85° C. and the pressure was adjusted to 150 mbar. Subsequently, the volatile constituents were removed, again under reduced pressure, and 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 (5.97 g) with a molecular weight of 376.3 g/mol (C14H18BrNO4S).

後処理

  1. customAfter the removal of the solvent under reduced pressure (bath temperature 70° C.)
  2. customthe viscous residue was dried at 50° C. in a vacuum
  3. customdrying cabinet for 16 hours
  4. waitTherefore, the oily residue was left
  5. customto react on the rotary evaporator under reduced pressure (bath temperature 80° C.) for 4 hours
  6. temperaturethe bath temperature was increased to 85° C.
  7. customSubsequently, the volatile constituents were removed, again under reduced pressure
  8. customthe crude product was purified by means of normal phase chromatography
  9. concentrationconcentrated by rotary evaporation

出典と根拠

ORDレコード
ord-484259611b6c4b75a5e256bacff921d5
出典データセット
uspto-grants-2014_11
特許番号
US08895547B2

関連ノート

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