m-Chloroperbenzoic acid → HCID 90010405, compound

HRID 1056607Notes

Reaction equation

HRID 1056607 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][N+:7]([O-])=[C:6]([C:11]2[O:12][C:13](=[O:17])[N:14]([CH3:16])[N:15]=2)[CH:5]=1)[CH3:2].C(OC1C=CN=C(C2OC(=O)N(C)N=2)C=1)C.C1C=C([Cl:40])C=C(C(OO)=O)C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:40][C:8]1[N:7]=[C:6]([C:11]2[O:12][C:13](=[O:17])[N:14]([CH3:16])[N:15]=2)[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[CH:9]=1

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 90010466HCID 90010466, compoundHCID 90010545HCID 90010545, compound

Product 1

HCID 90010405HCID 90010405, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step-4: 4-Ethoxy-2-(4-methyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)pyridine1-oxide: A solution of 5-(4-ethoxypyridin-2-yl)-3-methyl-1,3,4-oxadiazol-2(3H)-one (200 mg, 0.90 mmol) and mCPBA (156 mg, 0.90 mmol) in DCM (5 mL) was stirred at RT for 48 h. Ice water (10 mL) was added to the above reaction mixture, basified with aqueous saturated sodium bicarbonate solution (5 mL) and extracted with ethylacetate (3×10 mL). The combined organic layers were washed with brine (10 mL), dried (Na2SO4) and filtered. The filtrate was concentrated under vacuum to afford 160 mg (75%) of title compound as a white solid. 1HNMR (400 MHz, DMSO) δ 8.29 (d, J=5.5 Hz, 1H), 7.32 (d, J=2.5 Hz, 1H), 7.13 (dd, J=5.5 & 2.5 Hz, 1H), 4.16 (q, J=7.0 Hz, 2H), 3.42 (s, 3H), 1.32 (t, J=7.0 Hz, 3H); GC-MS (m/z) 237 (M)+.

Workup

  1. extractionextracted with ethylacetate (3×10 mL)
  2. washThe combined organic layers were washed with brine (10 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-6dd7f3f723274cc2ba3ba190cee6eceb
Source dataset
uspto-grants-2016_07
Patent number
US09399638B2

Reaction notes

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