Ammonium Hydroxide → 1,5-diethyl-1H-pyrazole-3-carboxamide

HRID 1984342Notes

Reaction equation

HRID 1984342 reaction equation
[CH2:1]([N:3]1[C:7]([CH2:8][CH3:9])=[CH:6][C:5]([C:10]([O:12]CC)=O)=[N:4]1)[CH3:2].[OH-].[NH4+:16]>>[CH2:1]([N:3]1[C:7]([CH2:8][CH3:9])=[CH:6][C:5]([C:10]([NH2:16])=[O:12])=[N:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 22145420Ethyl 1,5-diethylpyrazole-3-carboxylate

Product 1

HCID 669585351,5-diethyl-1H-pyrazole-3-carboxamide

Procedure

A mixture of ethyl 1,5-diethyl-1H-pyrazole-3-carboxylate (29.4 g, 0.50 mol) and ammonium hydroxide (150 mL of 30%) was stirred overnight at ambient temperature. An analysis by thin layer chromatography (TLC) indicated the reaction was incomplete. The reaction was then heated for 14 hours at 125° C. in a pressure vessel, allowed to cool to ambient temperature, and cooled to 0° C. A precipitate formed, was isolated by filtration, and washed with cold hexanes to provide 8.3 g of 1,5-diethyl-1H-pyrazole-3-carboxamide as a white solid, mp 129-131° C.

Workup

  1. temperatureThe reaction was then heated for 14 hours at 125° C. in a pressure vessel
  2. temperatureto cool to ambient temperature
  3. temperaturecooled to 0° C
  4. customA precipitate formed
  5. customwas isolated by filtration
  6. washwashed with cold hexanes

Sources & evidence

ORD record
ord-22aa986d65324142990d2f6325dd6a24
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

Loading…