Ammonia → 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-Pyrazole-3-carboxamide

HRID 254821Notes

Reaction equation

HRID 254821 reaction equation
[NH3:1].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])[N:12]=[C:11]([C:22](Cl)=[O:23])[C:10]=2[CH3:25])=[CH:5][CH:4]=1>C(Cl)Cl>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])[N:12]=[C:11]([C:22]([NH2:1])=[O:23])[C:10]=2[CH3:25])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 152841395-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carbonyl chloride

Product 1

HCID 668441705-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-Pyrazole-3-carboxamideYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (1.3 ml, 22.0 mmol) was added to a solution of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid (2.09 g, 5.5 mmol) in toluene (50 ml) maintained at room temperature. The mixture was refluxed at 110° C. for 2 hours and then cooled to room temperature. The resulting solution was evaporated and dried under a vacuum to produce crude 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl chloride, which are not further purified. 27% aqueous ammonia (2 ml) was added to the solution of crude 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl chloride in methylene chloride (10 ml) at 0° C. After stirring 3 hours at room temperature, the resulting solution was quenched with saturated ammonium chloride which was extracted twice with 50 ml portions of ethyl acetate. After concentrating the extract by evaporation, the crude residue was purified using a silica gel column (hexane/ethyl acetate=1/1), to obtain the title compound (2.07 g, 99%) as white solid.

Workup

  1. customthe resulting solution was quenched with saturated ammonium chloride which
  2. extractionwas extracted twice with 50 ml portions of ethyl acetate
  3. concentrationAfter concentrating the
  4. extractionextract by evaporation
  5. customthe crude residue was purified

Sources & evidence

ORD record
ord-04ccdb9f28724fce82b966eda2c66808
Source dataset
uspto-grants-2011_01
Patent number
US07875647B2

Reaction notes

Loading…