2,6-Dimethoxybenzoyl chloride → HCID 178491374, compound

HRID 2292301Notes

Reaction equation

HRID 2292301 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-53a311ea3241420fb7f67be789f2464a
Source dataset
uspto-grants-1989_01
Patent number
US04801718

Reaction notes

Loading…