Phosphorus oxychloride → HCID 68663808, 화합물

HRID 452610

반응식

HRID 452610 반응식
[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

참가 물질

5

반응물 4

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 27374893-(3-Fluorophenyl)propionic acidHCID 68663380HCID 68663380, 화합물

생성물 1

HCID 68663808HCID 68663808, 화합물수율 69%

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0fb9fbefbca142c0bdd18cb622ebc4a1
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492378B2

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