Hydrochloric Acid → HCID 18630148, compound

HRID 2188185Notes

Reaction equation

HRID 2188185 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.C(N(CC)CC)C.[CH2:13]([N:15]=[C:16]=[O:17])[CH3:14].Cl>C1COCC1.C(OCC)(=O)C>[CH2:13]([NH:15][C:16]([N:1]1[CH:5]=[CH:4][CH:3]=[N:2]1)=[O:17])[CH3:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1048PyrazoleHCID 8022Ethyl isocyanateHCID 8471Triethylamine

Product 1

HCID 18630148HCID 18630148, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of pyrazole (1.7 g, 25 mmol) and 4 mL triethylamine in 50 mL dry THF was added ethyl isocyanate (2 g, 28 mmol) at 0° C. and the resulting reaction solution was stirred at RT for 18 h. Ethyl acetate and 2N HCl were added. The aq layer was separated and extracted with ethyl acetate. The combined ethyl acetate layers were washed with brine, dried and concentrated in vacuo to give an oil. The oil was triturated with cold hexane to give 2.5 g of N-ethyl-1H-pyrazole-1-carboxamide as a white solid.

Workup

  1. customthe resulting reaction solution
  2. customThe aq layer was separated
  3. extractionextracted with ethyl acetate
  4. washThe combined ethyl acetate layers were washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customto give an oil
  8. customThe oil was triturated with cold hexane

Sources & evidence

ORD record
ord-3c806f584f34403fa208b3c55afc6b84
Source dataset
uspto-grants-2002_06
Patent number
US06410558B1

Reaction notes

Loading…