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

HRID 570342Notes

Reaction equation

HRID 570342 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-4461e0029b324fcdb2c23058864ffa7e
Source dataset
uspto-grants-2015_05
Patent number
US09023839B2

Reaction notes

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