Dimethyl Sulfoxide → Methylthiomethyl p-tolyl sulfone

HRID 1086108ノート

反応式

HRID 1086108 の反応式
[CH3:1][S:2]([CH3:4])=O.C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+].[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([S:23]([O-:25])=[O:24])=[CH:19][CH:18]=1.[Na+]>[Cl-].[Na+].O.C(O)(=O)C>[CH3:1][S:2][CH2:4][S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:26])=[CH:18][CH:19]=1)(=[O:25])=[O:24]

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 2723791Sodium p-toluenesulfinate

生成物 1

HCID 548421Methylthiomethyl p-tolyl sulfone収率 34%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

Dimethylsulfoxide (9.25 g, 118 mmol) and acetic anhydride (15.6 g, 153 mmol) were heated to 80° C. for 24 hours. The reaction solution was cooled to room temperature, then glacial acetic acid (90 ml), sodium acetate (9.7 g, 118 mmol) and sodium p-toluenesulfinate (31.6 g, 178 mmol, dried in vacuo overnight with P2O5 at 50° C.) were added. The mixture was heated to 100° C. for 24 hours. Brine (150 ml) was added and the solution was extracted with methylene chloride (5X, 100 ml). The organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give a gummy solid. The solid was recrystallized from 95% ethanol (3B) to yield 8.68 g of white crystals of (methylthio)(p-toluenesulfonyl)methane: m.p. 81°-83° C.

後処理

  1. temperatureThe mixture was heated to 100° C. for 24 hours
  2. extractionthe solution was extracted with methylene chloride (5X, 100 ml)
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a gummy solid
  8. customThe solid was recrystallized from 95% ethanol (3B)

出典と根拠

ORDレコード
ord-eaabfa6b5c2d44e48310a6ef70333eff
出典データセット
uspto-grants-1991_04
特許番号
US05011938

反応ノート

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