Sodium Hydroxide → HCID 135738567, compound

HRID 1532062Notes

Reaction equation

HRID 1532062 reaction equation
[CH2:1]([O:3][C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[C:6]([NH:8][C:9]1[N:13]([CH2:14][CH2:15][CH3:16])[N:12]=[CH:11][C:10]=1[C:17]([NH2:19])=[O:18])=O)[CH3:2].[OH-].[Na+]>O.C(O)C>[CH2:1]([O:3][C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[C:6]1[NH:19][C:17](=[O:18])[C:10]2[CH:11]=[N:12][N:13]([CH2:14][CH2:15][CH3:16])[C:9]=2[N:8]=1)[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53883132HCID 53883132, compound

Product 1

HCID 135738567HCID 135738567, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 5-(2-ethoxybenzamido)-1-n-propyl-pyrazole-4-carboxamide (Preparation 2; 0.541 g, 0.0017 mol) and sodium hydroxide (0.10 g, g, 0.0026 mol) in a mixture of water (5 ml) and ethanol 1 ml) was heated under reflux for 20 hours. The cool reaction solution was extracted with dichloromethane (5×30 ml), then the combined extracts dried (Na2SO4) and evaporated under vacuum to give the crude product. Purification by column chromatography (SiO2, 5% MeOH in CH2Cl2) afforded the title compound as a white solid (0.45 g, 89%). Crystallisation of a sample from ethyl acetate-hexane gave colourless needles, m.p. 154-155° C. Found: C,64.45; H,5.97; N,18.89. C16H18N4O2 requires C,64.41; H,6.08; N,18.78%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hours
  3. customThe cool reaction solution
  4. extractionwas extracted with dichloromethane (5×30 ml)
  5. dry with materialthe combined extracts dried (Na2SO4)
  6. customevaporated under vacuum
  7. customto give the crude product
  8. customPurification by column chromatography (SiO2, 5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-264540e867dc4cc6ba2442fadcb1cd1a
Source dataset
uspto-grants-2001_03
Patent number
US06200980B1

Reaction notes

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