Sodium Chloride → 2-(2-Methyl-2-trifluoromethyl-6-phenylsulfonyl-3,4-dihydro-2H-1,4-benzoxazin-4-yl)pyridine-N-oxide

HRID 1940507

Reaktionsgleichung

Reaktionsgleichung von HRID 1940507
[CH3:1][C:2]1([C:21]([F:24])([F:23])[F:22])[CH2:7][NH:6][C:5]2[CH:8]=[C:9]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:10]=[CH:11][C:4]=2[O:3]1.Cl[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N+:27]=1[O-:32].Cl.[H-].[Na+].[OH-].[Na+].[Cl-].[Na+]>CS(C)=O.C(OCC)(=O)C.CO.C(OCC)(=O)C>[CH3:1][C:2]1([C:21]([F:24])([F:22])[F:23])[CH2:7][N:6]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N+:27]=2[O-:32])[C:5]2[CH:8]=[C:9]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:10]=[CH:11][C:4]=2[O:3]1

Komponenten

9

Edukt 5

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 88478Chloride 2-chloropyridinium 1-oxideHCID 214625712-methyl-2-trifluoromethyl-6-phenylsulfonyl-3,4-dihydro-2H-1,4-benzoxazine

Produkt 1

HCID 103664882-(2-Methyl-2-trifluoromethyl-6-phenylsulfonyl-3,4-dihydro-2H-1,4-benzoxazin-4-yl)pyridine-N-oxideAusbeute 43,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 21584119Ethylacetate methanolLösungsmittel

Versuchsvorschrift

A solution of 2-methyl-2-trifluoromethyl-6-phenylsulfonyl-3,4-dihydro-2H-1,4-benzoxazine (200 mg) and 2-chloropyridine N-oxide·HCl (121 mg;) in dimethylsulfoxide (8 mL) was treated with sodium hydride (60% dispersion in oil, 58 mg), and stirred under a nitrogen atmosphere for 18 hours. The mixture was then poured into a solution containing aqueous sodium hydroxide (0.5 N, 150 mL) and saturated sodium chloride (20 mL.) and extracted with ethyl acetate. (3×150 mL). The combined organic portions were washed with aqueous sodium hydroxide (0.5 N, 30 mL) and saturated sodium chloride (5 mL) and evaporated to yield a black semi-solid. Chromatography of this solid on silica gel eluting with ethyl acetate then ethyl acetate/methanol (97:3) yielded the title compound (110 mg) as a white solid; mp 192°-193° C.; NMR (250 MHz, d6-DMSO): 1.55 (s,3), 3.98 (dd,2), 6.8.1 (s,1), 7.20 (d,1), 7.40 (dd, 1), 7.45 (m,2), 7.62 (m,4) 7.85 (dd,2), 8.42 (d, 1); MS: m/z=451(M+1). Analysis for C21H17F3N2O4S: Calculated: C, 56.00; H, 3.78; N, 6.22; Found: C, 56.10; H, 3.88; N, 6.02.

Aufarbeitung

  1. additionThe mixture was then poured into a solution
  2. extractionextracted with ethyl acetate
  3. washThe combined organic portions were washed with aqueous sodium hydroxide (0.5 N, 30 mL) and saturated sodium chloride (5 mL)
  4. customevaporated
  5. customto yield a black semi-solid

Quellen und Nachweise

ORD-Eintrag
ord-298299fc415d4f3fbab3dd8fea880b65
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05700798

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