Pyridine → Phenyl 3-cyano-4-(ethylsulfonyl)phenylcarbamate

HRID 735558노트

반응식

HRID 735558 반응식
[C:1]1([O:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[CH:13]=[CH:14][C:15]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])=[C:16]([CH:19]=1)[C:17]#[N:18].N1C=CC=CC=1>C(Cl)Cl>[C:17]([C:16]1[CH:19]=[C:12]([NH:11][C:8](=[O:9])[O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:13]=[CH:14][C:15]=1[S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])#[N:18]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 598380375-Amino-2-(ethanesulfonyl)benzonitrile

생성물 1

HCID 68818495Phenyl 3-cyano-4-(ethylsulfonyl)phenylcarbamate수율 85%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Phenylchloroformate (0.63 mL, 5 mmol) was added dropwise to a solution of 6B in methylene chloride (10 mL) and pyridine (0.60 mL, 7.1 mmol) at 0° C. After stirring for 1 h, the reaction mixture was partitioned between 1.0 M HCl (150 mL) and EtOAc (150 mL). The layers were separated and the organic phase was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (0% to 100% EtOAc in hexanes) to yield 25A (1.34 g, 85%) as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm 1.32 (t, J=7.45 Hz, 3 H) 3.36 (q, J=7.33 Hz, 2 H) 7.14-7.21 (m, J=7.58 Hz, 2 H) 7.26-7.31 (m, J=7.45, 7.45 Hz, 1 H) 7.37-7.45 (m, J=7.83, 7.83 Hz, 2 H) 7.66 (bs, 1 H) 7.83 (dd, J=8.72, 2.15 Hz, 1 H).

후처리

  1. customthe reaction mixture was partitioned between 1.0 M HCl (150 mL) and EtOAc (150 mL)
  2. customThe layers were separated
  3. washthe organic phase was washed with saturated NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (0% to 100% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-f797af9a6dd54bbcb04b5416b86c9a92
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592331B2

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