Aspirin → 4-Isothiocyanatophenyl 2-acetoxybenzoate

HRID 44171

반응식

HRID 44171 반응식
[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]

참가 물질

7

반응물 4

HCID 2244AspirinHCID 10868DicyclohexylcarbodiimideHCID 3082127Desmethylanethol trithioneHCID 178418300HCID 178418300, 화합물

생성물 1

HCID 250657714-Isothiocyanatophenyl 2-acetoxybenzoate수율 7%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7f65cfde5e3e4cd1be0d862d3f8b9bd1
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541398B2

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