Hydrochloric Acid → HCID 58764016, compound

HRID 2387162Notes

Reaction equation

HRID 2387162 reaction equation
[CH:1]1([C:4]2[N:8]([CH3:9])[N:7]=[C:6]([CH:10](OCC)[O:11]CC)[N:5]=2)[CH2:3][CH2:2]1.Cl.[OH-].[Na+]>>[CH:1]1([C:4]2[N:8]([CH3:9])[N:7]=[C:6]([CH:10]=[O:11])[N:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58764114HCID 58764114, compound

Product 1

HCID 58764016HCID 58764016, compoundYield 61.9%

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-32c04d7d57bb4666a90290919396c042
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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