Water → N-Benzyl-N-(2-cyano-6-trifluoromethyl-phenyl)-4-methoxy-benzenesulfonamide

HRID 583331

Reaktionsgleichung

Reaktionsgleichung von HRID 583331
[CH2:1]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].F[C:23]1[C:30]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:28]=[CH:27][C:24]=1[C:25]#[N:26].O>CN(C=O)C>[CH2:1]([N:8]([C:23]1[C:30]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:28]=[CH:27][C:24]=1[C:25]#[N:26])[S:9]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5189742-Fluoro-3-(trifluoromethyl)benzonitrileHCID 741351N-benzyl-4-methoxybenzenesulfonamide

Produkt 1

HCID 17866657N-Benzyl-N-(2-cyano-6-trifluoromethyl-phenyl)-4-methoxy-benzenesulfonamideAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 3.05 g (11.0 mmol) of the product of Example 121 in 15 mL of DMF was added 0.484 g (12.1 mmol) of 60% sodium hydride. The resulting mixture was stirred for 30 min at room temperature and then 1.89 g (10.0 mmol) of 2-fluoro-3-(trifluoromethyl)benzonitrile in 2 mL of DMF was added. The reaction mixture was stirred at 90° C. for 18 hr, poured into water and extracted with ether. The combined organics were washed with water, brine, dried over MgSO4, filtered and concentrated in vacuo. The crude solid was triturated with ether to provide 3.33 g (75%) of the desired product as a white solid. Electrospray Mass Spec 447.2(M+H).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at 90° C. for 18 hr
  2. extractionextracted with ether
  3. washThe combined organics were washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude solid was triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-aa9bade4cfae4e3ca0736770c4211ab4
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05929097

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