Sodium hydride → 2-(2-Ethyl-2-trifluoromethyl-6-nitro-3,4-dihydro-2H-1,4-benzoxazine-4-yl)pyridine-N-oxide

HRID 375524노트

반응식

HRID 375524 반응식
[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]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 88478Chloride 2-chloropyridinium 1-oxideHCID 214625692-ethyl-2-trifluoromethyl-6-nitro-3,4-dihydro-2H-1,4-benzoxazine

생성물 1

HCID 214625702-(2-Ethyl-2-trifluoromethyl-6-nitro-3,4-dihydro-2H-1,4-benzoxazine-4-yl)pyridine-N-oxide수율 35%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4bf7d2431d7f45b4a7e2a2eeab8a5352
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05486515

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