Methylamine → N-Methyl-1-(p-tolyl)-5-(4-chlorophenyl)-1H-pyrazole-3-carboxamide

HRID 55358Notes

Reaction equation

HRID 55358 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)=[CH:11][C:10]([C:20](Cl)=[O:21])=[N:9]2)=[CH:4][CH:3]=1.C(Cl)Cl.[CH3:26][NH2:27]>C(O)C>[CH3:26][NH:27][C:20]([C:10]1[CH:11]=[C:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[N:9]=1)=[O:21]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 6344DichloromethaneHCID 54331566HCID 54331566, compound

Product 1

HCID 19957364N-Methyl-1-(p-tolyl)-5-(4-chlorophenyl)-1H-pyrazole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.50 g of 1-(4-methylphenyl)-5-(4-chlorophenyl)pyrazole-3-carboxylic acid chloride in ml of CH2Cl2 is added dropwise to 100 ml of a 33% solution of methylamine in ethanol. After stirring for hours at room temperature, the mixture is concentrated under vacuum, the residue is taken up with a mixture of 5% Na2CO3 +AcOEt, the organic phase is decanted, washed with a saturated solution of NaCl and dried over MgSO4 and the solvents are evaporated off. The residue is taken up in isopropyl ether and the crystals obtained are filtered off and dried under vacuum to give 0.44 g of the expected amide.

Workup

  1. concentrationthe mixture is concentrated under vacuum
  2. additionthe residue is taken up with a mixture of 5% Na2CO3 +AcOEt
  3. customthe organic phase is decanted
  4. washwashed with a saturated solution of NaCl
  5. dry with materialdried over MgSO4
  6. customthe solvents are evaporated off
  7. customthe crystals obtained
  8. filtrationare filtered off
  9. customdried under vacuum

Sources & evidence

ORD record
ord-8de981eb7b8446c1be8ea774e7329d62
Source dataset
uspto-grants-1997_04
Patent number
US05624941

Reaction notes

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