Aspirin → 4-(3-Thioxo-3H-1,2-dithiol-5-yl)phenyl 2-acetoxybenzoate

HRID 18628

反応式

HRID 18628 の反応式
[C:1]([O:4][C:5]1[C:6](=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].OC1C2N=NNC=2C=CC=1.C1CCC(N=C=NC2CCCCC2)CC1.O[C:40]1[CH:45]=[CH:44][C:43]([C:46]2[S:50][S:49][C:48](=[S:51])[CH:47]=2)=[CH:42][CH:41]=1>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([O:9][C:40]1[CH:41]=[CH:42][C:43]([C:46]2[S:50][S:49][C:48](=[S:51])[CH:47]=2)=[CH:44][CH:45]=1)=[O:8])(=[O:3])[CH3:2]

参加物

7

反応物 4

HCID 2244AspirinHCID 10868DicyclohexylcarbodiimideHCID 3082127Desmethylanethol trithioneHCID 178418300HCID 178418300、化合物

生成物 1

HCID 117180344-(3-Thioxo-3H-1,2-dithiol-5-yl)phenyl 2-acetoxybenzoate収率 40%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To the solution of 1 (acetylsalicylic acid, 416 mg, 2.31 mmol) in 40 mL of dimethylformamide, hydroxybenzotriazole (343 mg, 2.54 mmol) and DCC (523 mg, 2.54 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 5-p-hydroxyphenyl-1,2-dithiole-3-thione (2; 574 mg, 2.54 mmol) was added and stirred for 1 h at 0° C. and 3 h at room temperature. After filtration, the filtrate was evaporated under reduced pressure to remove the solvent. The oily residue thus obtained was dissolved in ethyl acetate; the organic layer was washed with brine, dried on anhydrous MgSO4, filtered and the solvent evaporated. The crude product was loaded on a silica gel open column and eluted with ethyl ether/petroleum ether (1/1), from which 4-(5-thioxo-5H-1,2-dithiol-3-yl)phenyl 2-acetoxybenzoate (3) was obtained (354 mg, 40% yield).

後処理

  1. stirringstirred for 1 h at 0° C. and 3 h at room temperature
  2. filtrationAfter filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. customto remove the solvent
  5. customThe oily residue thus obtained
  6. washthe organic layer was washed with brine
  7. dry with materialdried on anhydrous MgSO4
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. washeluted with ethyl ether/petroleum ether (1/1), from which 4-(5-thioxo-5H-1,2-dithiol-3-yl)phenyl 2-acetoxybenzoate (3)
  11. customwas obtained (354 mg, 40% yield)

出典と根拠

ORDレコード
ord-0784ea4004a047fb97965e31f554cde6
出典データセット
uspto-grants-2010_06
特許番号
US07741359B2

関連ノート

読み込み中…