Water → 5-chloro-1-methyl-3-trifluoromethyl-N-(1,1-dimethylindane-4-yl)pyrazole-4-carboxamide

HRID 1252164Notes

Reaction equation

HRID 1252164 reaction equation
[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[C:6]([NH2:11])[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.N1C=CC=CC=1.[Cl:19][C:20]1[N:24]([CH3:25])[N:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[C:21]=1[C:30](Cl)=[O:31].O>C1(C)C=CC=CC=1>[Cl:19][C:20]1[N:24]([CH3:25])[N:23]=[C:22]([C:26]([F:28])([F:27])[F:29])[C:21]=1[C:30]([NH:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH2:4][CH2:3][C:2]2([CH3:12])[CH3:1])=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 27945855-Chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbonyl chlorideHCID 131156151,1-Dimethyl-2,3-dihydro-1H-inden-4-amine

Product 1

HCID 139207215-chloro-1-methyl-3-trifluoromethyl-N-(1,1-dimethylindane-4-yl)pyrazole-4-carboxamideYield 81.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 1.61 g of 1,1-dimethyl-4-aminoindane and 2 ml of pyridine in 50 ml of toluene was added drop by drop with stirring at room temperature a solution of 2.47 g of 5-chloro-1-methyl-3-trifluoromethylpyrazole-4-carboxylic acid chloride in 10 ml of toluene, followed by stirring at room temperature for 12 hours. Thereafter, the reaction solution was poured into a cold water to result in separation into two layers. The aqueous layer was extracted with ethyl acetate. The resultant organic layer was dried over anhydrous magnesium sulfate and the soluent was distilled off. The residue was recrystallized using toluene to obtain 3.01 g of 5-chloro-1-methyl-3-trifluoromethyl-N-(1,1-dimethylindane-4-yl)pyrazole-4-carboxamide having a melting point of 119.9° C.

Workup

  1. customto result in separation into two layers
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe resultant organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe soluent was distilled off
  5. customThe residue was recrystallized

Sources & evidence

ORD record
ord-a8d03a69425d4a02b93aee7f9c20ed2b
Source dataset
uspto-grants-1988_05
Patent number
US04742074

Reaction notes

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