Dicyclohexylcarbodiimide → 4-(Isothiocyano)-phenyl 2-(2-methoxynaphthalen-6-yl)propanoate

HRID 18635

反応式

HRID 18635 の反応式
[CH3:1][C@H:2]([C:15]([OH:17])=[O:16])[C:3]1[CH:8]=[CH:7][C:6]2[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:5]=2[CH:4]=1.O[C:19]1[C:27]2N=N[NH:24][C:23]=2[CH:22]=[CH:21][CH:20]=1.C1CCC(N=C=NC2CCCCC2)CC1.OC1C=CC(C2S[S:53][C:52](=S)C=2)=CC=1>CN(C)C=O.C(OCC)(=O)C>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:5]2[C:6](=[CH:7][CH:8]=[C:3]([CH:2]([CH3:1])[C:15]([O:17][C:20]3[CH:21]=[CH:22][C:23]([N:24]=[C:52]=[S:53])=[CH:27][CH:19]=3)=[O:16])[CH:4]=2)[CH:9]=1

参加物

7

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 156391NaproxenHCID 3082127Desmethylanethol trithioneHCID 178418300HCID 178418300、化合物

生成物 1

HCID 250657694-(Isothiocyano)-phenyl 2-(2-methoxynaphthalen-6-yl)propanoate収率 21%

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 (naproxene, 691 mg, 3 mmol) in 20 mL of dimethylformamide, hydroxybenzotriazole (446 mg, 3.3 mmol) and DCC (619 mg, 3.3 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 4-hydroxyphenylisothiocyanate (2; 500 mg, 3.3 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 dichloromethane, from which 4-(isothiocyano)-phenyl 2-(2-methoxynaphthalen-6-yl)propanoate (3) was obtained (230 mg, 21% 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 dichloromethane, from which 4-(isothiocyano)-phenyl 2-(2-methoxynaphthalen-6-yl)propanoate (3)
  9. customwas obtained (230 mg, 21% yield)

出典と根拠

ORDレコード
ord-ff81df212f994bafbf6c7bfe90e1cc54
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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