Pyrazole → Methyl (5-tert-butyl-1H-pyrazol-3-yl)carbamate

HRID 615809Notes

Reaction equation

HRID 615809 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[NH:4][N:3]=1.N1C=CC=N1.Cl[C:17]([O:19][CH3:20])=[O:18].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)(Cl)Cl>[C:7]([C:5]1[NH:4][N:3]=[C:2]([NH:1][C:17](=[O:18])[O:19][CH3:20])[CH:6]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 1048PyrazoleHCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 5227873-Amino-5-tert-butylpyrazole2×

Product 1

HCID 13469501Methyl (5-tert-butyl-1H-pyrazol-3-yl)carbamateYield 26.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

10 g of 3-amino-5-t-butylpyrazole as prepared in Reference Example (this pyrazole compound being hereinafter referred to as "Compound [II]") was dissolved in 100 ml of carbon tetrachloride, and 6.8 g of methyl chloroformate was added to the solution. The mixture was then allowed to react for 5 hours under refluxing. After cooling the reaction solution, a potassium carbonate aqueous solution was added thereto whereby crystals were formed. The crystals were collected by filtration, and washed with carbon tetrachloride and water to obtain 3.8 g of methyl N-(5-t-butyl-3-pyrazolyl)carbamate. This compound was recrystallized from a mixed solvent of carbon tetrachloride and chloroform and found to have a melting point of 177° C.

Workup

  1. customto react for 5 hours
  2. temperatureunder refluxing
  3. temperatureAfter cooling the reaction solution
  4. customwhereby crystals were formed
  5. filtrationThe crystals were collected by filtration
  6. washwashed with carbon tetrachloride and water

Sources & evidence

ORD record
ord-e91c6fe96a9642a5a48384cf49a8d376
Source dataset
uspto-grants-1985_02
Patent number
US04501606

Reaction notes

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