Methanol → HCID 178521956, compound

HRID 1935329Notes

Reaction equation

HRID 1935329 reaction equation
[NH2:1][C:2]1[N:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])[N:5]=[C:4]([CH:16]2[CH2:18][CH2:17]2)[CH:3]=1.CO.C1(N=C=O)C=CC=CC=1.[OH-].[Na+]>>[CH:16]1([C:4]2[CH:3]=[C:2]([NH:6][C:7]([NH:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:8])[NH:1][N:5]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 4

HCID 887MethanolHCID 7672Phenyl isocyanateHCID 14798Sodium HydroxideHCID 12049758HCID 12049758, compound

Product 1

HCID 178521956HCID 178521956, compoundYield 20.6%

Procedure

To 5-amino-3-cyclopropyl-N-phenyl-1H-pyrazole-l-carboxamide (0.5 g, 2 mmol) in 6 ml of methanol 0.5 ml (4.6 mmol)of phenylisocyanate and 2 ml of 10% NaOH were added. The mixture was refluxed for about 2h, then cooled, quenched with 10% HCl and extracted with ethyl acetate. The organic phase was washed with 10% HCl, water and brine. Concentration and chromatography on silica gel, eluting with 8% to 20% acetone in methylene chloride, afforded 100 mg (20% yield) of N-(3-cyclopropyl-1H-pyrazol-5-yl)-N′-phenylurea as a colorless, glassy solid.

Workup

  1. temperaturecooled
  2. customquenched with 10% HCl
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with 10% HCl, water and brine
  5. concentrationConcentration and chromatography on silica gel
  6. washeluting with 8% to 20% acetone in methylene chloride

Sources & evidence

ORD record
ord-8e150c84c9394a33b30224abcf893d04
Source dataset
uspto-grants-2002_05
Patent number
US06387900B1

Reaction notes

Loading…