Potassium Hydroxide → HCID 178495595, compound

HRID 1032374Notes

Reaction equation

HRID 1032374 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][N:5](O)[CH:6]=1.[OH-:8].[K+].Br[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](=[CH:23][O:24][CH3:25])[C:19]([O:21][CH3:22])=[O:20]>C(O)C.CN(C)C=O>[Cl:1][C:2]1[C:3]([O:8][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18](=[CH:23][O:24][CH3:25])[C:19]([O:21][CH3:22])=[O:20])=[N:4][NH:5][CH:6]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 133912524-Chloro-1H-pyrazol-1-olHCID 53395349Methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoate

Product 1

HCID 178495595HCID 178495595, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

2.4 g (0.02 mol) of 4-chloro-1-hydroxypyrazole in 30 ml of ethanol are added dropwise to a solution of 1.2 g (0.02 mol) of potassium hydroxide in 50 ml of ethanol. The reaction mixture is stirred at room temperature for two hours and then concentrated. The residue is taken up in 60 ml of dimethylformamide, and 5.7 g (0.02 mol) of methyl α-(2-bromomethylphenyl)-β-methoxyacrylate in 30 ml of dimethylformamide are added. The mixture is stirred at 100° C. for two hours, a solvent is removed under reduced pressure and the residue is taken up in methyl tertbutyl ether. The organic phase is washed with water, dried and concentrated. 5.0 g (77%) of the title compound are obtained as an oil (compound no. 9).

Workup

  1. concentrationconcentrated
  2. stirringThe mixture is stirred at 100° C. for two hours
  3. customa solvent is removed under reduced pressure
  4. washThe organic phase is washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7185e3ffd15740eb97b88d274fab1b78
Source dataset
uspto-grants-1990_09
Patent number
US04957937

Reaction notes

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