Dimethylamine → HCID 15672063, compound

HRID 1086755Notes

Reaction equation

HRID 1086755 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[C:13]([Cl:25])=[CH:14][C:15]([Cl:24])=[C:16]([CH:23]=2)[O:17][CH:18]([CH3:22])[C:19](Cl)=[O:20])=[N:4][N:5]([CH3:11])[C:6]=1[O:7][CH:8]([F:10])[F:9].[CH3:26][NH:27][CH3:28].N1C=CC=N1.C(OCC)(=O)C>O1CCCC1>[CH3:26][N:27]([CH3:28])[C:19](=[O:20])[CH:18]([O:17][C:16]1[CH:23]=[C:12]([C:3]2[C:2]([Cl:1])=[C:6]([O:7][CH:8]([F:10])[F:9])[N:5]([CH3:11])[N:4]=2)[C:13]([Cl:25])=[CH:14][C:15]=1[Cl:24])[CH3:22]

Participants

6

Reactant 4

HCID 674Dimethylamine2×HCID 1048PyrazoleHCID 8857Ethyl AcetateHCID 15030575HCID 15030575, compound

Product 1

HCID 15672063HCID 15672063, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-[5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazole-3-yl)-2,4-dichlorophenoxy]propionyl chloride (0.80 g, 1.78 mmoles) in 20 ml anhydrous tetrahydrofuran was added dropwise to a solution of 50% dimethylamine (0.32 g, 3.56 mmoles) in 20 ml tetrahydrofuran at room temperature to react the pyrazole derivative with dimethylamine. After the addition was finished, the reaction was continued further for 1 hour. Then ethyl acetate was added to the reaction product solution, and the mixture was washed with water. The separated organic layer was dehydrated, concentrated under reduced pressure, and purified by silica gel chromatography, giving crystals (0.24 g) of the title compound, m.p. 148.9° C., yield 27%.

Workup

  1. additionAfter the addition
  2. washthe mixture was washed with water
  3. concentrationconcentrated under reduced pressure
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-d31b2f7b66a0447982cef10c8df4b55c
Source dataset
uspto-grants-1991_07
Patent number
US05032165

Reaction notes

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