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

HRID 1984384Notes

Reaction equation

HRID 1984384 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. Found: C, 61.32; H, 9.04; N, 21.71.

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-9f25341edba940e5aee5b827ab2e6441
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

Loading…