Methanol → 5-ethyl-1-butyl-1H-pyrazole-3-carboxamide

HRID 2283784Notes

Reaction equation

HRID 2283784 reaction equation
[CH2:1]([C:3]1[N:7]([CH2:8][CH2:9][CH2:10][CH3:11])[N:6]=[C:5]([C:12]([O:14]CC)=O)[CH:4]=1)[CH3:2].CO.[OH-].[NH4+:20]>>[CH2:1]([C:3]1[N:7]([CH2:8][CH2:9][CH2:10][CH3:11])[N:6]=[C:5]([C:12]([NH2:20])=[O:14])[CH:4]=1)[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 66958154ethyl 5-ethyl-1-butyl-1H-pyrazole-3-carboxylate

Product 1

HCID 669586575-ethyl-1-butyl-1H-pyrazole-3-carboxamide

Procedure

Ethyl 5-ethyl-1-butyl-1H-pyrazole-3-carboxylate (13.27 g, 59.2 mmol) in concentrated ammonium hydroxide (50 mL) was heated at 125° C. for 14 hours in a pressure vessel. After the vessel was allowed to cool to ambient temperature, methanol (40 mL) was added and the vessel was heated at 125° C. for 1 day. After cooling to ambient temperature, the vessel was cooled in an ice bath and the product began to crystallize from the reaction mixture. Two crops of crystals were isolated to provide 5.50 g of 5-ethyl-1-butyl-1H-pyrazole-3-carboxamide as off-white crystals, mp 60-61° C. MS (APCI) m/z 196.1 (M+H)+; Anal. calcd for C10H17N3O: C, 61.51; H, 8.78; N, 21.52.

Workup

  1. temperaturethe vessel was heated at 125° C. for 1 day
  2. temperatureAfter cooling to ambient temperature
  3. temperaturethe vessel was cooled in an ice bath
  4. customto crystallize from the reaction mixture
  5. customTwo crops of crystals were isolated

Sources & evidence

ORD record
ord-77d20528024c4cf7bcad15903b749044
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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