Sodium hydride → HCID 21462570, compound

HRID 375524

Reaction equation

HRID 375524 reaction equation
[H-].[Na+].[CH2:3]([C:5]1([C:18]([F:21])([F:20])[F:19])[CH2:10][NH:9][C:8]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:7]=2[O:6]1)[CH3:4].Cl.Cl[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N+:25]=1[O-:30]>CS(C)=O>[CH2:3]([C:5]1([C:18]([F:21])([F:20])[F:19])[CH2:10][N:9]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N+:25]=2[O-:30])[C:8]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:7]=2[O:6]1)[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 88478Chloride 2-chloropyridinium 1-oxideHCID 21462569HCID 21462569, compound

Product 1

HCID 21462570HCID 21462570, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydride (0.68 g, 60% in mineral oil) was added to a solution of 2-ethyl-2-trifluoromethyl-6-nitro-3,4-dihydro-2H-1,4-benzoxazine (0.235 g), 2-chloropyridine-N-oxide hydrochloride (0.142 g), and dimethylsulfoxide (10 mL) and stirred at room temperature overnight. The mixture was quenched with saturated ammonium chloride/water and extracted into ethyl acetate. The organic extract was washed (water, brine) dried, decolorized (charcoal), filtered (celite) and evaporated. Chromatography, eluting successively with dichloromethane, ethyl acetate, and then methanol, gave the title compound as a yellow solid (0.11 g); mp 59°-62° C.; NMR: 0.95 (t,3), 2.04 (q), 4.05 (d,d), 7.01 (s,1), 7.25 (d) 7.45 (m,2), 7.63 (d), 7.76 (d), 8.41 (d,1); MS: m/z=370(M+1). Analysis for C16H14F3N3O4 : Calculated: C, 52.04; H, 3.82; N, 11.38; Found: C, 51.95; 3.98; N, 11.10.

Workup

  1. customThe mixture was quenched with saturated ammonium chloride/water
  2. extractionextracted into ethyl acetate
  3. extractionThe organic extract
  4. washwas washed (water, brine)
  5. customdried
  6. filtrationfiltered (celite)
  7. customevaporated
  8. washChromatography, eluting successively with dichloromethane, ethyl acetate

Sources & evidence

ORD record
ord-4bf7d2431d7f45b4a7e2a2eeab8a5352
Source dataset
uspto-grants-1996_01
Patent number
US05486515

Linked notes

Loading…