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

HRID 2421103노트

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HRID 2421103 반응식
[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

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 16722585HCID 16722585, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-dd8df703e7134904804081992952983b
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07956074B2

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