Water → 5,7-Dimethyl-6-(nitromethylsulphonyl)thiachroman-1,1-dioxide

HRID 2081811ノート

反応式

HRID 2081811 の反応式
C(OO)(=[O:3])C.[CH3:6][C:7]1[C:16]([S:17][CH2:18][N+:19]([O-:21])=[O:20])=[C:15]([CH3:22])[CH:14]=[C:13]2[C:8]=1[CH2:9][CH2:10][CH2:11]S2.S([S:27]([O-:29])=[O:28])([O-])(=O)=O.[Na+].[Na+].[OH2:32]>C(O)(=O)C.C(Cl)(Cl)Cl>[CH3:6][C:7]1[C:16]([S:17]([CH2:18][N+:19]([O-:21])=[O:20])(=[O:3])=[O:32])=[C:15]([CH3:22])[CH:14]=[C:13]2[C:8]=1[CH2:9][CH2:10][CH2:11][S:27]2(=[O:28])=[O:29]

参加物

7

反応物 4

HCID 962WaterHCID 6585Peracetic Acid2 回HCID 656671Sodium PyrosulfiteHCID 570022415,7-Dimethyl-6-(nitromethylthio)thiachroman

生成物 1

HCID 678275245,7-Dimethyl-6-(nitromethylsulphonyl)thiachroman-1,1-dioxide収率 47%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6212Chloroform溶媒

反応条件

温度
60 °C

実験手順

A 35% w/v solution of peracetic acid in acetic acid (3.2 ml) was added in a slow stream to a stirred solution of 5,7-dimethyl-6-(nitromethylthio)thiachroman (500 mg, 1.86 mM) in chloroform (25 ml). The solution was then stirred and heated at 60° C. Two further quantities of 35% w/v peracetic acid solution (3.2 ml) were added after 2 hours and 3.5 hours, respectively. After 7.5 hours, the reaction mixture was cooled and a solution of sodium metabisulphite (5 g) in water (50 ml) was added slowly with further cooling. The organic layer was separated and the aqueous layer extracted with chloroform. The combined extracts were dried (Na2SO4) and evaporated. The white solid obtained was recrystallised from toluene to give 5,7-dimethyl-6-(nitromethylsulphonyl)thiachroman-1,1-dioxide (290 mg, 47% yield), m.p. 168°-170° C.; NMR: (d6 -DMSO): 2.38(2H,m), 2.56(3H,s), 2.65(3H,s), 2.91(2 H,t), 3.55(2H,m), 6.65(2H,s), 7.79(1H,s); microanalysis, found: C,43.3; H,4.1; N,4.1%; C12H15NO6S2 requires: C,43.2; H,4.5; N,4.2%.

後処理

  1. additionwere added after 2 hours and 3.5 hours
  2. temperaturethe reaction mixture was cooled
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with chloroform
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. customevaporated
  7. customThe white solid obtained
  8. customwas recrystallised from toluene

出典と根拠

ORDレコード
ord-a27c45b85b314295a943e569c2ebd66b
出典データセット
uspto-grants-1993_02
特許番号
US05185452

反応ノート

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