Hydrogen Peroxide → HCID 90010639, compound

HRID 1056609Notes

Reaction equation

[CH2:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[O:13][C:12](=[O:14])[N:11]([CH3:15])[N:10]=1)[CH3:2].C(OC(=O)C1C=CN=CC=1CC)C.C(C1C=[N+]([O-])C=CC=1C1OC(=O)N(C)N=1)C.OO.C(=O)([O-])[O-].[K+].[K+].C(Cl)[Cl:54]>C(O)(=O)C>[Cl:54][C:6]1[CH:7]=[C:8]([C:9]2[O:13][C:12](=[O:14])[N:11]([CH3:15])[N:10]=2)[C:3]([CH2:1][CH3:2])=[CH:4][N:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Step-2: 5-(3-Ethylpyridin-4-yl)-3-methyl-1,3,4-oxadiazol-2(3H)-one: The title compound was prepared from ethyl-3-ethylisonicotinate by following the similar procedure sequentially as described instep-2, step-3 and step-4 of Intermediate-1a. 1HNMR (400 MHz, CDCl3) δ 8.63 (s, 1H), 8.59 (d, J=5.0 Hz, 1H), 7.64 (d, J=5.0 Hz, 1H), 3.56 (s, 3H), 3.03 (q, J=7.5 Hz, 2H), 1.28 (t, J=7.5 Hz, 3H); GC-MS (m/z) 205 (M)+ Step-3: 3-Ethyl-4-(4-methyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)pyridine-1-oxide: To a stirred solution of step-2 intermediate (3.50 g, 17.1 mmol) in acetic acid (30 mL) was added hydrogen peroxide (0.62 mL, 20.4 mmol) drop-wise at RT and the resulting mixture was heated to 80° C. and maintained for 12 h. The reaction was cooled to RT and basified with solid potassium carbonate. The resulting slurry was diluted with DCM (50 mL) and filtered. The filtrate was concentrated under vacuum to afford 2.70 g (70%) of the title compound as white solid. GC-MS (m/z) 221 (M)+.

Workup

temperaturemaintained for 12 h
filtrationfiltered
concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record: ord-2c60b0e813174a0da7b8d40ecb413bc6
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399638B2

Reaction notes

Loading…