Dimethylformamide → HCID 66489407, compound

HRID 1748465Notes

Reaction equation

HRID 1748465 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.CN(C)C=O.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:25]([CH3:26])=[C:24]([C:27]([OH:29])=[O:28])[CH:23]=[N:22]2)=[CH:17][CH:16]=1>O>[CH3:1][O:28][C:27]([C:24]1[CH:23]=[N:22][N:21]([C:18]2[CH:17]=[CH:16][C:15]([Cl:14])=[CH:20][CH:19]=2)[C:25]=1[CH3:26])=[O:29]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 27771661-(4-chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 66489407HCID 66489407, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium carbonate (8.76 g) and methyl iodide (3.15 ml) were added to a N,N-dimethylformamide solution (42 ml) of 1-(4-chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid (10.0 g) in Reference Example 3 at room temperature and stirred for five hours. Potassium carbonate (4.08 g) and methyl iodide (2.1 ml) were subsequently added and the mixture was stirred further for three hours at room temperature. After completion of the reaction, water (200 ml) was added and the precipitated solid was collected by filtration to give 1-(4-chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid methyl ester (10.5 g) as a pale yellow solid.

Workup

  1. stirringthe mixture was stirred further for three hours at room temperature
  2. additionwas added
  3. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-2a27071363c840a5a3b4e3216fb393b9
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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