Trityl chloride → Dimethyl 1-trityl-3,5-pyrazoledicarboxylate

HRID 262344

Reaction equation

HRID 262344 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[NH:7][N:6]=1)=[O:4].[H-].[Na+].[H][H].[C:18]1([C:24](Cl)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.O.O.CN(C=O)C>[C:18]1([C:24]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:7]2[C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:9][C:5]([C:3]([O:2][CH3:1])=[O:4])=[N:6]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 14844913,5-dimethyl 1H-pyrazole-3,5-dicarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 12377531Dimethyl 1-trityl-3,5-pyrazoledicarboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

To a solution of 1.84 g. (10 mmol) of 3,5-pyrazoledicarboxylic acid dimethyl ester* in 15 ml. of DMF, stirred at 0° under argon, was added 480 mg. (10 mmol) of 50% NaH (suspension in mineral oil). After the evolution of hydrogen had ceased, 2.7 g. (10 mmol) of triphenylmethyl chloride in 20 ml. of DMF was added dropwise. The mixture was allowed to warm to room temperature, stirred 1.5 hours, poured into H2O, and the resulting precipitate filtered. After recrystallization from 2-ethoxyethanol-H2O, there was obtained the end product. The analytical sample was obtained as colorless needles by recrystallization from DMF-H2O; mp 212°-213.5°.

Workup

  1. additionwas added 480 mg
  2. filtrationthe resulting precipitate filtered
  3. customAfter recrystallization from 2-ethoxyethanol-H2O
  4. customthere was obtained the end product

Sources & evidence

ORD record
ord-031af27ee6244fe5b4bbed57f3a65bb4
Source dataset
uspto-grants-1979_05
Patent number
US04153799

Linked notes

Loading…