2,6-Dimethoxybenzoyl chloride → HCID 178491374, compound

HRID 980108Notes

Reaction equation

HRID 980108 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:11][O:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[C:14]=1[C:15](Cl)=[O:16]>C1C=CC=CC=1>[CH3:2][C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:15](=[O:16])[C:14]2[C:18]([O:22][CH3:23])=[CH:19][CH:20]=[CH:21][C:13]=2[O:12][CH3:11])[NH:7][N:6]=1)([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 748102,6-Dimethoxybenzoyl chlorideHCID 178441179HCID 178441179, compound

Product 1

HCID 178491374HCID 178491374, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of 1.39 g of 3-tert.-butyl-5-amino-1H-pyrazole in 50 ml of benzene were added in one portion 2.01 g of 2,6-dimethoxybenzoyl chloride. The reaction mixture was heated at reflux for sixteen hours. The reaction mixture was then cooled, filtered, and the solvent was removed from the filtrate by evaporation. The residue was crystallized from ethyl acetate to provide 550 mg of N-[3-(1,1-dimethylethyl)-1H-pyrazol-5-yl]-2,6-dimethoxybenzamide.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for sixteen hours
  3. temperatureThe reaction mixture was then cooled
  4. filtrationfiltered
  5. customthe solvent was removed from the filtrate by evaporation
  6. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-3b973d429ed74d5daa137523c059580a
Source dataset
uspto-grants-1987_01
Patent number
US04636243

Reaction notes

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