Water → 1,3,5-trimethyl-N-(1,1,3-trimethyl-4-indanyl)pyrazole-4-carboxamide

HRID 1252168Notes

Reaction equation

HRID 1252168 reaction equation
[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[C:6]([NH2:11])[CH:7]=[CH:8][CH:9]=2)[CH:4]([CH3:12])[CH2:3]1.C(N(CC)CC)C.[CH3:21][N:22]1[C:26]([CH3:27])=[C:25]([C:28](Cl)=[O:29])[C:24]([CH3:31])=[N:23]1.O>O1CCCC1>[CH3:21][N:22]1[C:26]([CH3:27])=[C:25]([C:28]([NH:11][C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:5]=2[CH:4]([CH3:12])[CH2:3][C:2]3([CH3:13])[CH3:1])=[O:29])[C:24]([CH3:31])=[N:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 112175411,1,3-Trimethylindan-4-amineHCID 13637622trimethyl-1H-pyrazole-4-carbonyl chloride

Product 1

HCID 141278841,3,5-trimethyl-N-(1,1,3-trimethyl-4-indanyl)pyrazole-4-carboxamideYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.75 g of 1,1,3-trimethyl-4-aminoindane and 2 ml of triethylamine in 50 ml of tetrahydrofuran was with stirring at room temperature added dropwise a solution of 1.73 g of 1,3,5-trimethylpyrazole-4-carboxylic acid chloride in 10 ml of tetrahydrofuran, followed by stirring at room temperature for 12 hours. Then, the reaction solution was poured into a cold water to result in separation into two layers. The aqueous layer was extracted with ethyl acetate and the organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off. The residue was recrystallized with toluene to obtain 2.55 g of 1,3,5-trimethyl-N-(1,1,3-trimethylindane-4-yl)pyrazole-4-carboxamide (mp 176.2° C.).

Workup

  1. stirringby stirring at room temperature for 12 hours
  2. customto result in separation into two layers
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was recrystallized with toluene

Sources & evidence

ORD record
ord-c9097da69842428890625a7e69773623
Source dataset
uspto-grants-1988_05
Patent number
US04742074

Reaction notes

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