Water → 1,3-Dimethyl-4-(2,4-dichlorobenzoyl)-5-trichloroacryloyloxy pyrazole

HRID 1388237Notes

Reaction equation

HRID 1388237 reaction equation
[CH3:1][N:2]1[C:6]([OH:7])=[C:5]([C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])[C:4]([CH3:18])=[N:3]1.C(N(CC)CC)C.[Cl:26][C:27]([Cl:33])=[C:28]([Cl:32])[C:29](Cl)=[O:30].O>C1C=CC=CC=1>[CH3:1][N:2]1[C:6]([O:7][C:29](=[O:30])[C:28]([Cl:32])=[C:27]([Cl:33])[Cl:26])=[C:5]([C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])[C:4]([CH3:18])=[N:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 131532,3,3-Trichloro-2-propenoyl chlorideHCID 178434070HCID 178434070, compound

Product 1

HCID 132078581,3-Dimethyl-4-(2,4-dichlorobenzoyl)-5-trichloroacryloyloxy pyrazoleYield 74.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

2.85 g of 1,3-dimethyl-4-(2,4-dichlorobenzoyl)-5-hydroxy pyrazole and 1.01 g of triethylamine were dissolved in 20 ml of benzene. 1.94 g of trichloroacrylic acid chloride were dropped into the solution. The reaction mixture was stirred for 3 hours at the reflux temperature of benzene. After the completion of the reaction, water was added to the reaction mixture, the organic layer was separated and dried. Benzene was distilled off under reduced pressure to give 3.3 g of 1,3-dimethyl-4-(2,4-dichlorobenzoyl)-5-trichloroacryloyloxy pyrazole as colorless crystals of melting point 141° to 142° C.

Workup

  1. additionwas added to the reaction mixture
  2. customthe organic layer was separated
  3. customdried
  4. distillationBenzene was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7dd29a1f6787401f8e74a381a47bfffc
Source dataset
uspto-grants-1984_02
Patent number
US04431441

Reaction notes

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