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

HRID 735558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 735558
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-f797af9a6dd54bbcb04b5416b86c9a92
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592331B2

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