Stannous chloride dihydrate → 5-(5-(Azetidin-1-yl)-1,2,4-oxadiazol-3-yl)-2-methylaniline

HRID 405826노트

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HRID 405826 반응식
[N:1]1([C:5]2[O:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([N+:17]([O-])=O)[CH:11]=3)[N:6]=2)[CH2:4][CH2:3][CH2:2]1.O.O.Cl[Sn]Cl>C(O)C>[N:1]1([C:5]2[O:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([CH:11]=3)[NH2:17])[N:6]=2)[CH2:4][CH2:3][CH2:2]1

참가 물질

4

반응물 2

HCID 61436Stannous chloride dihydrateHCID 712815105-(Azetidin-1-yl)-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole

생성물 1

HCID 866774565-(5-(Azetidin-1-yl)-1,2,4-oxadiazol-3-yl)-2-methylaniline수율 65%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a stirred solution of 5-(azetidin-1-yl)-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole (108) (1.4 g, 5.38 mmol) in ethanol (25 mL) was added SnCl2.2H2O (6.07 g, 26.90 mmol). The resulting solution was stirred for 20 min at reflux then cooled to room temperature and concentrated under vacuum. The residue was poured into saturated sodium hydroxide (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (3×250 mL), dried over anhydrous sodium sulfate, concentrated under vacuum and purified by flash chromatography (PE/EA=10:1) to afford 5-(5-(azetidin-1-yl)-1,2,4-oxadiazol-3-yl)-2-methylaniline (109) (0.8 g, 65% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.28-7.36 (m, 2H), 7.12 (d, J=7.8 Hz, 1H), 4.32 (t, J=7.5 Hz, 4H), 3.69 (brs, 2H), 2.47-2.57 (m, 2H), 2.21 (s, 3H). MS m/z 231.1 (M+1)+.

후처리

  1. temperatureat reflux
  2. concentrationconcentrated under vacuum
  3. additionThe residue was poured into saturated sodium hydroxide (50 mL)
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. washThe combined organic layers were washed with brine (3×250 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. custompurified by flash chromatography (PE/EA=10:1)

출처 및 근거

ORD 기록
ord-afa670a8bc684a849c1b091d841eb190
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754071B2

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