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

HRID 1940507노트

반응식

HRID 1940507 반응식
[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

참가 물질

9

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매HCID 21584119Ethylacetate methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-298299fc415d4f3fbab3dd8fea880b65
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05700798

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