Ammonium Hydroxide → HCID 66958785, compound

HRID 1984336Notes

Reaction equation

HRID 1984336 reaction equation
[CH2:1]([N:8]1[C:12]([CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:11][C:10]([C:17]([O:19]CC)=O)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[NH4+:23]>CO>[CH2:1]([N:8]1[C:12]([CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:11][C:10]([C:17]([NH2:23])=[O:19])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 66958280HCID 66958280, compound

Product 1

HCID 66958785HCID 66958785, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 1-benzyl-5-(2-methylpropyl)-1H-pyrazole-3-carboxylate (30 g) in methanol (60 mL) was treated with ammonium hydroxide (60 mL) according to a modification of the method described in Part D of Examples 1-4. The reaction was heated for 14 hours. At the end of the reaction, the methanol was removed under reduced pressure, and the remaining solution was extracted with tert-butyl methyl ether (3×). The combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Toluene was added twice and removed under reduced pressure to remove residual water. Hexane was added to the residue; crystals formed and were isolated by filtration, washed with hexane, and air-dried overnight to provide 6.93 g of 1-benzyl-5-(2-methylpropyl)-1H-pyrazole-3-carboxamide as small, off-white crystals.

Workup

  1. temperatureThe reaction was heated for 14 hours
  2. customAt the end of the reaction
  3. customthe methanol was removed under reduced pressure
  4. extractionthe remaining solution was extracted with tert-butyl methyl ether (3×)
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. additionToluene was added twice
  9. customremoved under reduced pressure
  10. customto remove residual water
  11. additionHexane was added to the residue
  12. customcrystals formed
  13. customwere isolated by filtration
  14. washwashed with hexane
  15. customair-dried overnight

Sources & evidence

ORD record
ord-4aef588a64574f7e9cd5a59a6d672f58
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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