Trityl chloride → HCID 57941469, compound

HRID 1437861Notes

Reaction equation

HRID 1437861 reaction equation
[C:1]1([C:7](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:21][C:22]([F:34])([F:33])[C:23]1[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][NH:25][N:24]=1.C(N(CC)CC)C>CN(C)C=O>[CH2:31]([O:30][C:28]([C:27]1[C:23]([C:22]([F:33])([F:34])[F:21])=[N:24][N:25]([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:26]=1)=[O:29])[CH3:32]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178469923HCID 178469923, compound

Product 1

HCID 57941469HCID 57941469, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triphenylmethyl chloride (1.1 g, 3.6 mmol) was added to a solution of ethyl 3-(trifluoromethyl)-pyrazole-4-carboxylate (0.75 g, 3.6 mmol) and triethylamine (1 mL, 7.2 mmol) in N,N-dimethylformamide (12 mL). This mixture was stirred at room temperature overnight, then the solvent was evaporated and the residue was diluted with water (30 mL) and extracted with ethyl acetate. The organic extract was washed with water and brine, dried (magnesium sulfate), filtered, evaporated, and chromatographed (10% ethyl acetate/petroleum ether) to give 3-trifluoromethyl-1-trityl-1H-pyrazole-4-carboxylic acid ethyl ester (1.28 g, 79%).

Workup

  1. customthe solvent was evaporated
  2. additionthe residue was diluted with water (30 mL)
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water and brine
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated
  9. customchromatographed (10% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-8221d40d03ca44ac8bd92278bbd032d6
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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