Sodium Carbonate → 4-Chloropyrazol-1-yl 3,3-dimethylacrylate

HRID 652696Notes

Reaction equation

HRID 652696 reaction equation
[CH3:1][C:2]([CH3:7])=[CH:3][C:4](Cl)=[O:5].[Cl:8][C:9]1[CH:10]=[N:11][N:12]([OH:14])[CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH3:1][C:2]([CH3:7])=[CH:3][C:4]([O:14][N:12]1[CH:13]=[C:9]([Cl:8])[CH:10]=[N:11]1)=[O:5]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 1023943-Methyl-2-butenoyl chlorideHCID 133912524-Chloro-1H-pyrazol-1-ol

Product 1

HCID 135482284-Chloropyrazol-1-yl 3,3-dimethylacrylateYield 90.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

20 g of dimethylacrylyl chloride, dissolved in 100 g of acetonitrile, are added to 20 g of 4-chloro-1-hydroxypyrazole, 20 g of sodium carbonate and 150 g of acetonitrile at 25° C., while stirring. Stirring is continued for 12 hours at 25° C., after which the solid product is filtered off under suction and washed with 100 g of acetonitrile. The solution is evaporated down at 40° C. and under 20 mbar, the residue is taked up in 200 g of dichloromethane, the solution is extracted 3 times with 200 g of saturated aqueous sodium bicarbonate solution, the organic phase is dried with magnesium sulfate and evaporated down, and the residue is digested with 300 g of petroleum ether. 30.5 g (90% of theory) of 4-chloropyrazol-1-yl 3,3-dimethylacrylate of melting point 71° C. are obtained.

Workup

  1. stirringStirring
  2. filtrationafter which the solid product is filtered off under suction
  3. washwashed with 100 g of acetonitrile
  4. customThe solution is evaporated down at 40° C. and under 20 mbar
  5. extractionthe solution is extracted 3 times with 200 g of saturated aqueous sodium bicarbonate solution
  6. dry with materialthe organic phase is dried with magnesium sulfate
  7. customevaporated down

Sources & evidence

ORD record
ord-9af35dcc4c4b4247ab3518cfe0ba3db0
Source dataset
uspto-grants-1987_06
Patent number
US04673429

Reaction notes

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