Aspirin → 4-Isothiocyanatophenyl 2-acetoxybenzoate

HRID 18637

反応式

HRID 18637 の反応式
[CH3:1][C:2]([O:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=1[C:11]([OH:13])=[O:12])=[O:3].O[C:15]1[C:23]2N=N[NH:20][C:19]=2[CH:18]=[CH:17][CH:16]=1.C1CCC(N=C=NC2CCCCC2)CC1.OC1C=CC(C2S[S:49][C:48](=S)C=2)=CC=1>CN(C)C=O.C(OCC)(=O)C>[C:2]([O:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=1[C:11]([O:13][C:16]1[CH:17]=[CH:18][C:19]([N:20]=[C:48]=[S:49])=[CH:23][CH:15]=1)=[O:12])(=[O:3])[CH3:1]

参加物

7

反応物 4

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

生成物 1

HCID 250657714-Isothiocyanatophenyl 2-acetoxybenzoate収率 7%

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 (aspirin, 1200 mg, 6.67 mmol) in 60 mL of dimethylformamide, hydroxybenzotriazole (992 mg, 7.34 mmol) and DCC (1520 mg, 7.34 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 4-hydroxyphenylisothiocyanate (2; 1109 mg, 7.34 mmol) was added and stirred for 1 h at 0° C. and 2 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 and the precipitate was removed. The solvent was evaporated and the crude product was loaded on a silica gel open column and eluted with chloroform/n-hexane 6:4, from which 4-isothiocyanatophenyl 2-acetoxybenzoate (3) was obtained (150 mg, 7% yield).

後処理

  1. stirringstirred for 1 h at 0° C. and 2 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. customthe precipitate was removed
  7. customThe solvent was evaporated
  8. washeluted with chloroform/n-hexane 6:4, from which 4-isothiocyanatophenyl 2-acetoxybenzoate (3)
  9. customwas obtained (150 mg, 7% yield)

出典と根拠

ORDレコード
ord-82e8209838fc4bbe987e45849aab02d8
出典データセット
uspto-grants-2010_06
特許番号
US07741359B2

関連ノート

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