Potassium Carbonate → HCID 13823795, compound

HRID 1193432Notes

Reaction equation

HRID 1193432 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([Cl:18])[C:9]=1[N:19]1[C:23]([NH2:24])=[C:22]([N+:25]([O-:27])=[O:26])[CH:21]=[N:20]1.Br[CH:29]([CH3:34])[C:30]([O:32][CH3:33])=[O:31]>C(#N)C>[Cl:7][C:8]1[CH:13]=[C:12]([C:14]([F:16])([F:17])[F:15])[CH:11]=[C:10]([Cl:18])[C:9]=1[N:19]1[C:23]([NH:24][CH:29]([CH3:34])[C:30]([O:32][CH3:33])=[O:31])=[C:22]([N+:25]([O-:27])=[O:26])[CH:21]=[N:20]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 175845Nipyraclofen

Product 1

HCID 13823795HCID 13823795, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2.8 g (0.02 mole) of potassium carbonate are added to 3.4 g (0.01 mole) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-4-nitro-5-amino-pyrazole, dissolved in 30 ml of acetonitrile, and 3.7 g (0.022 mole) of methyl α-bromopropionate, dissolved in 10 ml of acetonitrile, are added dropwise at room temperature in the course of 10 minutes. The reaction mixture is heated under reflux for 21/2 hours and filtered hot and the solvent and excess α-bromopropionate are removed by concentration of the filtrate in vacuo. The residue is crystallized from petroleum ether. 3.8 g (88% of theory) of methyl α-{N-[1-(2,6-dichloro-4-trifluoromethyl-phenyl)-4-nitro-pyrazol-5-yl]amino}-propionate of melting point 123° C.-130° C. are obtained.

Workup

  1. additionare added dropwise at room temperature in the course of 10 minutes
  2. temperatureThe reaction mixture is heated
  3. temperatureunder reflux for 21/2 hours
  4. filtrationfiltered hot
  5. customthe solvent and excess α-bromopropionate are removed by concentration of the filtrate in vacuo
  6. customThe residue is crystallized from petroleum ether

Sources & evidence

ORD record
ord-61ad698f8fa1433a856ce678dd1fa9a1
Source dataset
uspto-grants-1989_03
Patent number
US04810283

Reaction notes

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