Methanol → HCID 88365911、化合物

HRID 1737215ノート

反応式

HRID 1737215 の反応式
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](=[N:13][OH:14])[CH3:12].[H-].[Na+].Br[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=1[N:26]1[C:30](Cl)=[N:29][N:28]([CH3:32])[C:27]1=[O:33].[CH3:34][O-:35].[Na+].CO>O1CCCC1.C(OCC)(=O)C>[CH3:34][O:35][C:30]1[N:26]([C:20]2[C:19]([CH2:18][O:14][N:13]=[C:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)[CH3:12])=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:25])[C:27](=[O:33])[N:28]([CH3:32])[N:29]=1

参加物

8

反応物 5

HCID 887MethanolHCID 24758Sodium hydrideHCID 3185661-(naphthalen-2-yl)ethan-1-one oximeHCID 10942334Sodium MethoxideHCID 218419724-[2-(bromomethyl)-6-methylphenyl]-5-chloro-2,4-dihydro-2-methyl-3H-1,2,4-triazol-3-one

生成物 1

HCID 88365911HCID 88365911、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 1-(2-naphthalenyl)ethanone oxime (492 mg, 2.65 mmol) in tetrahydrofuran (7.5 mL) cooled to 0° C. under a nitrogen atmosphere was added 95% NaH (69 mg, 2.88 mmol) and the mixture was stirred for 20 min. The title compound of Step E (700 mg, 2.21 mmol) was then added to the reaction and the mixture was stirred at room temperature for 3 h. Sodium methoxide as a 30% solution in methanol (1.3 mL, 6.63 mmol) was added and the reaction mixture was heated to reflux for 10 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed with saturated ammonium chloride. The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel (25% ethyl acetate in hexanes as eluent) to give 306 mg of the title compound of Step F, a compound of the invention, as a golden oil. 1H NMR (CDCl3): δ 2.19 (s,3H), 2.32 (s,3H), 3.41 (s,3H), 3.89 (s,3H), 5.21 (AB q,2H), 7.30 (d,1H), 7.36-7.5 (m,4H), 7.8 (m,4H), 7.97 (s,1H).

後処理

  1. stirringthe mixture was stirred at room temperature for 3 h
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 10 h
  4. washwashed with saturated ammonium chloride
  5. dry with materialThe organic phase was dried (magnesium sulfate)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography on silica gel (25% ethyl acetate in hexanes as eluent)

出典と根拠

ORDレコード
ord-eba9c9ca04534a478b77d5dae7df4b53
出典データセット
uspto-grants-1999_10
特許番号
US05962436

反応ノート

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