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

HRID 375521

Reaction equation

HRID 375521 reaction equation
[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

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 754652-Chloropyridine oxideHCID 214625712-methyl-2-trifluoromethyl-6-phenylsulfonyl-3,4-dihydro-2H-1,4-benzoxazine

Product 1

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

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

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 (0.5N, 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 (0.5N, 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), 6.81 (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.

Workup

  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 (0.5N, 30 mL) and saturated sodium chloride (5 mL)
  4. customevaporated
  5. customto yield a black semi-solid

Sources & evidence

ORD record
ord-f74547fdf25a4592ab2731412a317ec9
Source dataset
uspto-grants-1996_01
Patent number
US05486515

Linked notes

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