4-Tert-Butylaniline → N-(4-(Tert-butyl)phenyl)-5-chloro-1-methyl-1H-pyrazole-4-carboxamide

HRID 2212696Notes

Reaction equation

HRID 2212696 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8](Cl)=[O:9].[C:11]([C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12]>C(Cl)Cl>[C:11]([C:15]1[CH:16]=[CH:17][C:18]([NH:19][C:8]([C:3]2[CH:4]=[N:5][N:6]([CH3:7])[C:2]=2[Cl:1])=[O:9])=[CH:20][CH:21]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 698614-Tert-ButylanilineHCID 27357735-Chloro-1-methyl-1H-pyrazole-4-carbonyl chloride

Product 1

HCID 86588705N-(4-(Tert-butyl)phenyl)-5-chloro-1-methyl-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-Chloro-1-methyl-1H-pyrazole-4-carbonyl chloride (1.0 g, 5.6 mmol) was dissolved in CH2Cl2 (100 mL) under N2 and cooled to 0° C. 4-t-Butylaniline was added and the reaction was stirred with gradual warming to RT overnight. The reaction was quenched with saturated NaHCO3(aq) and extracted 3× with fresh CH2Cl2. The CH2Cl2 extracts were washed with brine, combined, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure giving 5-chloro-1-methyl-1H-pyrazole-4-carboxylic acid (4-tert-butyl-phenyl)-amide as a foamy pink solid.

Workup

  1. temperaturewith gradual warming to RT overnight
  2. customThe reaction was quenched with saturated NaHCO3(aq)
  3. extractionextracted 3× with fresh CH2Cl2
  4. washThe CH2Cl2 extracts were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-df60249c14da415b9aff0e1d0140187c
Source dataset
uspto-grants-2006_09
Patent number
US07102009B2

Reaction notes

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