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Chlorodiphenylmethane → 1-(Diphenylmethyl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 131633
Notes
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Reaction equation

HRID 131633 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][NH:9][CH:10]=1)=[O:5])[CH3:2].[CH:11](Cl)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:10]=1)=[O:5])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7035ChlorodiphenylmethaneHCID 11430Potassium CarbonateHCID 142179ethyl 1H-pyrazole-4-carboxylate

Product 1

HCID 693134381-(Diphenylmethyl)-1H-pyrazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 13387
N-methyl-2-pyrrolidone
Solvent

Conditions

Temperature
100 °C

Procedure

A suspension of 1H-pyrazole-4-carboxylic acid ethyl ester (1.0 g), benzhydryl chloride (1.9 ml) and potassium carbonate (1.48 g) in anhydrous 1-methyl-2-pyrrolidinone (10 ml) was heated at 100° C. under nitrogen for 6 h. It was diluted with water and extracted with ethyl acetate, the organic extracts washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluting with i-hexane/ethyl acetate (4:1) followed by i-hexane/ethyl acetate (2:1) to give the sub-title compound (2.18 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic extracts washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography over silica
  7. washeluting with i-hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-b9eb24beb22d458e8dd7dc49124f29a9
Source dataset
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07384951B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes