Sodium hydride → HCID 73848365、化合物

HRID 1737208ノート

反応式

HRID 1737208 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]=[CH:21][C:20]=1[N:25]1[C:29]([O:30][CH3:31])=[N:28][N:27]([CH3:32])[C:26]1=[O:33]>CN(C=O)C>[CH3:31][O:30][C:29]1[N:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][O:14][N:13]=[C:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH3:12])[C:26](=[O:33])[N:27]([CH3:32])[N:28]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 3185661-(naphthalen-2-yl)ethan-1-one oximeHCID 110338324-[2-(Bromomethyl)phenyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one

生成物 1

HCID 73848365HCID 73848365、化合物収率 79%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 0.56 g (3.02 mmol) of 1-(2-naphthalenyl)ethanone oxime in 10 mL of DMF was added 0.13 g (3.28 mmol) of NaH. 0.75 (2.52 mmol) of the title compound of Step D was then added to the reaction and the mixture was stirred at room temperature for 3 h. The reaction mixture was washed successively with water and saturated NaCl and then extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography on silica gel using 60% ethyl acetate/hexane as eluent to give 0.80 g (79% yield) of the title compound of Step E, a compound of the invention, as a solid melting at 91-94° C.

後処理

  1. washThe reaction mixture was washed successively with water and saturated NaCl
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography on silica gel using 60% ethyl acetate/hexane as eluent

出典と根拠

ORDレコード
ord-bfa59fe4836a4827a5efe68e2fc92c2b
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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