Potassium Carbonate → Phenyl 5-phenylisoxazol-3-ylcarbamate

HRID 631384

반응식

HRID 631384 반응식
[C:1]1([C:7]2[O:11][N:10]=[C:9]([NH2:12])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13](=[O:16])([O-])[O-:14].[K+].[K+]>O1CCCC1>[C:1]1([C:7]2[O:11][N:10]=[C:9]([NH:12][C:13](=[O:16])[O:14][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

4

반응물 2

HCID 11430Potassium CarbonateHCID 36207925-Phenyl-1,2-oxazol-3-amine

생성물 1

HCID 59394374Phenyl 5-phenylisoxazol-3-ylcarbamate수율 160.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

5-Phenylisoxazol-3-amine (428 mg, 2.67 mmol) in tetrahydrofuran (4.8 mL) was treated with potassium carbonate (481 mg, 3.47 mmol) and phenyl choloroformate (0.67 mL, 5.3 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was filtered through a celite pad, washed with ethyl acetate and concentrated to dryness. The residue was taken into chloroform, washed with brine, and the organics dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography (hexane/ethyl acetate 8:2) to give phenyl 5-phenylisoxazol-3-ylcarbamate (599 mg, 80%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.92 (bs, 1H), 7.78 (d, 2H), 7.45 (m, 6H), 7.26 (m, 2H), 7.12 (s, 1H); LC-MS (ESI) m/z 281 (M+H)+.

후처리

  1. filtrationThe mixture was filtered through a celite pad
  2. washwashed with ethyl acetate
  3. concentrationconcentrated to dryness
  4. washwashed with brine
  5. dry with materialthe organics dried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate 8:2)

출처 및 근거

ORD 기록
ord-0b236e9b1cfa4e2e9753b78c47641366
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09320739B2

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