Dicyclohexylcarbodiimide → 4-(5-thioxo-5H-1,2-dithiol-3-yl)phenyl 2-(2-methoxynaphthalen-6-yl)propanoate

HRID 18630

반응식

HRID 18630 반응식
[CH3:1][C@H:2]([C:15]([OH:17])=[O:16])[C:3]1[CH:4]=[CH:5][C:6]2[CH:7]=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][C:11]=2[CH:12]=1.OC1C2N=NNC=2C=CC=1.C1CCC(N=C=NC2CCCCC2)CC1.O[C:44]1[CH:49]=[CH:48][C:47]([C:50]2[S:54][S:53][C:52](=[S:55])[CH:51]=2)=[CH:46][CH:45]=1>CN(C)C=O.C(OCC)(=O)C>[CH3:14][O:13][C:8]1[CH:9]=[CH:10][C:11]2[C:6](=[CH:5][CH:4]=[C:3]([CH:2]([CH3:1])[C:15]([O:17][C:44]3[CH:45]=[CH:46][C:47]([C:50]4[S:54][S:53][C:52](=[S:55])[CH:51]=4)=[CH:48][CH:49]=3)=[O:16])[CH:12]=2)[CH:7]=1

참가 물질

7

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 156391NaproxenHCID 3082127Desmethylanethol trithioneHCID 178418300HCID 178418300, 화합물

생성물 1

HCID 250659864-(5-thioxo-5H-1,2-dithiol-3-yl)phenyl 2-(2-methoxynaphthalen-6-yl)propanoate수율 36%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

To the solution of 1 (naproxen, 595 mg, 2.58 mmol) in 20 mL of dimethylformamide, hydroxybenzotriazole (388 mg, 2.87 mmol) and DCC (593 mg, 2.87 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 5-p-hydroxyphenyl-1,2-dithiole-3-thione (2; 650 mg, 2.87 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; the organic layer was washed with brine, with NaHCO3 5%, with citric acid 10% and than dried on anhydrous MgSO4, filtered and the solvent evaporated. The crude product was loaded on a silica gel open column and eluted with dichloromethane, from which 4-(5-thioxo-5H-1,2-dithiol-3-yl)phenyl 2-(2-methoxynaphthalen-6-yl)propanoate (3) was obtained (406 mg, 36% 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. washthe organic layer was washed with brine, with NaHCO3 5%, with citric acid 10%
  7. dry with materialthan dried on anhydrous MgSO4
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. washeluted with dichloromethane, from which 4-(5-thioxo-5H-1,2-dithiol-3-yl)phenyl 2-(2-methoxynaphthalen-6-yl)propanoate (3)
  11. customwas obtained (406 mg, 36% yield)

출처 및 근거

ORD 기록
ord-ed9d067180cb45dbad0b2c6c6c38e597
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741359B2

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