Phosphorus oxychloride → HCID 68663808、化合物

HRID 452610

反応式

HRID 452610 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=2[N+:20]([O-:22])=[O:21])[C:13]([NH:15][NH2:16])=[O:14])=[CH:5][CH:4]=1.[F:23][C:24]1[CH:25]=[C:26]([CH2:30][CH2:31][C:32](O)=O)[CH:27]=[CH:28][CH:29]=1.P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>>[F:23][C:24]1[CH:25]=[C:26]([CH2:30][CH2:31][C:32]2[O:14][C:13]([C:12]3[CH:17]=[CH:18][C:19]([N+:20]([O-:22])=[O:21])=[C:10]([CH:11]=3)[NH:9][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)=[N:15][N:16]=2)[CH:27]=[CH:28][CH:29]=1

参加物

5

反応物 4

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 27374893-(3-Fluorophenyl)propionic acidHCID 68663380HCID 68663380、化合物

生成物 1

HCID 68663808HCID 68663808、化合物収率 69%

反応条件

温度
100 °C

実験手順

A mixture of 3-[(4-methoxyphenyl)amino]-4-nitrobenzohydrazide (1.60 g, 5.29 mmol), 3-(3-fluorophenyl)propionic acid (0.89 g, 5.29 mmol) and phosphorus oxychloride (5.29 mL) was stirred at 100° C. for 2 hr. The reaction mixture was cooled to 0° C., neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=3/1) to give the title compound (1.51 g, yield 69%) as orange crystals.

後処理

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=3/1)

出典と根拠

ORDレコード
ord-0fb9fbefbca142c0bdd18cb622ebc4a1
出典データセット
uspto-grants-2013_07
特許番号
US08492378B2

関連ノート

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