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

HRID 1940507Notes

Reaction equation

HRID 1940507 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

9

Reactant 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

Product 1

HCID 103664882-(2-Methyl-2-trifluoromethyl-6-phenylsulfonyl-3,4-dihydro-2H-1,4-benzoxazin-4-yl)pyridine-N-oxideYield 43.6%

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 (0.5 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.

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

Sources & evidence

ORD record
ord-298299fc415d4f3fbab3dd8fea880b65
Source dataset
uspto-grants-1997_12
Patent number
US05700798

Reaction notes

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