Hydrochloric Acid → 3-Methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenylamine

HRID 1983093ノート

反応式

HRID 1983093 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]1[O:13][C:14]([C:17]2[C:18]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:19][O:20][C:21]=2[CH3:22])=[N:15][N:16]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C(O)C.[Fe]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[C:12]1[O:13][C:14]([C:17]2[C:18]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[N:19][O:20][C:21]=2[CH3:22])=[N:15][N:16]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 16722585HCID 16722585、化合物

生成物 1

HCID 167225873-Methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenylamine収率 43.3%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

To a suspension of 2-(2-methoxy-4-nitro-phenyl)-5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazole (200 mg, 0.53 mmol) in ethanol (2 mL) was added iron powder (148 mg, 2.64 mmol) and aqueous HCl (1 M, 0.53 mL, 0.53 mmol). The reaction mixture was stirred for 2 h at 90° C., cooled to ambient temperature and poured onto an aqueous solution of sodium carbonate (saturated, 20 mL) and ethyl acetate (20 mL) and then stirred for 1 h. Filtration over Hyflo® was followed by washing of the Hyflo® with ethyl acetate. The aqueous phase was extracted with ethyl acetate (20 mL). Drying over sodium sulfate, concentration and purification by chromatography (SiO2, heptane:ethyl acetate=50:50 to 0:100) afforded the title compound (80 mg, 43%) as a white solid. MS: m/e=349.2 [M+H]+.

後処理

  1. temperaturecooled to ambient temperature
  2. stirringstirred for 1 h
  3. filtrationFiltration over Hyflo®
  4. washby washing of the Hyflo® with ethyl acetate
  5. extractionThe aqueous phase was extracted with ethyl acetate (20 mL)
  6. dry with materialDrying over sodium sulfate, concentration and purification by chromatography (SiO2, heptane:ethyl acetate=50:50 to 0:100)

出典と根拠

ORDレコード
ord-77fdd9cf238c49f68a8ae8e00e1e37c2
出典データセット
uspto-grants-2009_06
特許番号
US07541372B2

反応ノート

読み込み中…