Ammonium hydroxide methanol → HCID 66958386, compound

HRID 1984374Notes

Reaction equation

HRID 1984374 reaction equation
[CH2:1]([C:5]1[N:9]([C:10]([CH3:13])([CH3:12])[CH3:11])[N:8]=[C:7]([C:14]([O:16]CC)=O)[CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[NH4+:20].CO>>[CH2:1]([C:5]1[N:9]([C:10]([CH3:13])([CH3:12])[CH3:11])[N:8]=[C:7]([C:14]([NH2:20])=[O:16])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 21894508Ammonium hydroxide methanolHCID 66958342HCID 66958342, compound

Product 1

HCID 66958386HCID 66958386, compound

Conditions

Temperature
125 °C

Procedure

Ethyl 5-butyl-1-tert-butyl-1H-pyrazole-3-carboxylate (60 g, 0.24 mol) in a 1:1 mixture of concentrated ammonium hydroxide/methanol (238 mL) was heated at 125° C. for 37 hours in a pressure vessel. After cooling to ambient temperature, the vessel was placed in an ice bath. The reaction mixture was stirred for 30 minutes, then was concentrated under reduced pressure to a brown oil. The oil was dissolved in dichloromethane and the solution was washed with water and brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give a wet brown solid. Hexanes were added, the mixture was stirred, and 18.67 g of 5-butyl-1-tert-butyl-1H-pyrazole-3-carboxamide was isolated by filtration as an off-white solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customthe vessel was placed in an ice bath
  3. concentrationwas concentrated under reduced pressure to a brown oil
  4. dissolutionThe oil was dissolved in dichloromethane
  5. washthe solution was washed with water and brine
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give a wet brown solid
  10. stirringthe mixture was stirred

Sources & evidence

ORD record
ord-527ea9d185944459945ae8d212c17d51
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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