Hydrochloric Acid → HCID 58764016, compound

In a 2 L round-bottomed flask containing the crude 5-cyclopropyl-3-(diethoxymethyl)-1-methyl-1H-1,2,4-triazole from Step 2, a solution of 2 N HCl (125 mL) was added and the reaction was allowed to stir at room temperature for 23 h, at which point, LC/MS analysis confirmed the formation of the aldehyde. The mixture was then treated with solid sodium hydroxide until a pH of 13 was obtained. The aqueous mixture was extracted with dichloromethane (3×150 mL), and the combined organic layers dried over sodium sulfate, filtered and the solvent evaporated under vacuum. The crude material was distilled Kugel-Rhor distillation at 135° C.–146° C. to afford 11.4 g (61.9%) the title product as a yellow-colored oil. This material contained 4.8 wt % of the self-condensed side-product, 3,5-dicyclopropyl-1-methyl-1H-1,2,4-triazole, by 1H NMR. 1H NMR (300 MHz, DMSO-d6): δ 0.96 (m, 2H), 1.10 (m, 2H), 2.22 (m, 1H), 4.00 (s, 3H), 9.78 (s, 1H). LC/MS (APCI) calcd for C7H9N3O: 151.07, found (M+H+): 152.1 m/z.

1. customwas obtained
2. extractionThe aqueous mixture was extracted with dichloromethane (3×150 mL)
3. dry with materialthe combined organic layers dried over sodium sulfate
4. filtrationfiltered
5. customthe solvent evaporated under vacuum
6. distillationThe crude material was distilled
7. distillationKugel-Rhor distillation at 135° C.–146° C.

ORD record

ord-28905134910f4a8ea37120a65988ec20

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07151105B2