Ethanol → HCID 178522953, compound

HRID 1935330Notes

Reaction equation

HRID 1935330 reaction equation
[CH:1]1([C:4]2[CH:8]=[C:7]([NH2:9])[NH:6][N:5]=2)[CH2:3][CH2:2]1.C(O)C.[Cl:13][C:14]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:15]=1[CH2:16][N:17]=[C:18]=[O:19].O>C(=O)([O-])O.[Na+]>[CH:1]1([C:4]2[CH:8]=[C:7]([NH:9][C:18]([NH:17][CH2:16][C:15]3[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:14]=3[Cl:13])=[O:19])[NH:6][N:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 46127082,4-Dichlorobenzyl isocyanateHCID 178507266HCID 178507266, compound

Product 1

HCID 178522953HCID 178522953, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

1 g (8.13 mmol) of 3-cyclopropyl-5-amino-1H-pyrazole are dissolved in 10 ml of ethanol containing 1.37 g (16.26 mmol) of sodium hydrogen carbonate and 3.27 g (16.26 mmol) of 2,4-dichlorobenzyl isocyanate. After 3 hours at room temperature 50 ml of water were added and the solid was filtered. The filtrate was evaporated to dryness and then redissolved with 10 ml of methanol. 8.2 ml of 1M sodium hydrate were added and the mixture stirred 4 h at room temperature. Methanol is evaporated and the residue is dissolved with dichloromethane and washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to afford 1.5 g (60% yield) of the title compound.

Workup

  1. filtrationthe solid was filtered
  2. customThe filtrate was evaporated to dryness
  3. dissolutionredissolved with 10 ml of methanol
  4. addition8.2 ml of 1M sodium hydrate were added
  5. customMethanol is evaporated
  6. dissolutionthe residue is dissolved with dichloromethane
  7. washwashed with water
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e24d23afae448fd8d4a231250d3702d
Source dataset
uspto-grants-2002_05
Patent number
US06387900B1

Reaction notes

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