Ethyl Acetate → N-(1-Methyl-1H-pyrazol-5-yl)urea

HRID 373437Notes

Reaction equation

HRID 373437 reaction equation
[O-:1][C:2]#[N:3].[Na+].[CH3:5][N:6]1[C:10]([NH2:11])=[CH:9][CH:8]=[N:7]1.C(OCC)(=O)C>O.C(O)(=O)C>[CH3:5][N:6]1[C:10]([NH:11][C:2]([NH2:3])=[O:1])=[CH:9][CH:8]=[N:7]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 1369272-Methyl-2H-pyrazol-3-ylamineHCID 517096Sodium Cyanate

Product 1

HCID 19812270N-(1-Methyl-1H-pyrazol-5-yl)ureaYield 52.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Procedure

A solution of sodium cyanate (52 g) in water (400 ml) was added dropwise to a solution of 1-methyl-5-aminopyrazole (19.4 g) in acetic acid (96 ml) and water (192 ml), and the mixture was stirred at ambient temperature for 7 hours. The reaction mixture was poured into a mixture of water (400 ml) and ethyl acetate (400 ml). The organic layer was separated, washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated to give 1-methyl-5-ureidopyrazole (14.6 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-3b420a7a24114ea9a88b7f9521d609d5
Source dataset
uspto-grants-1992_11
Patent number
US05162520

Reaction notes

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