HCID 15703507, compound → HCID 53762882, compound

HRID 1905401Notes

Reaction equation

HRID 1905401 reaction equation
[CH3:1][N:2]1[C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:5]([CH:14]=O)[CH:4]=[N:3]1.[NH2:16][O:17][CH2:18][C:19]1[CH:31]=[CH:30][C:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:21][CH:20]=1>C(O)C>[CH3:1][N:2]1[C:6]([O:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[C:5]([CH:14]=[N:16][O:17][CH2:18][C:19]2[CH:31]=[CH:30][C:22]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])=[CH:21][CH:20]=2)[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 15703507HCID 15703507, compoundHCID 200354391-Methyl-5-phenoxy-1H-pyrazole-4-carbaldehyde

Product 1

HCID 53762882HCID 53762882, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1.0 Gram (0.0049 mole) of 1-methyl-5-phenoxypyrazole-4-carbaldehyde and 1.1 g (0.0049 mole) of tert-butyl 4-aminooxymethylbenzoate were added to 20 ml of ethanol, and the resulting mixture was heated under reflux to carry out reaction. After completion of the reaction, ethanol was removed by evaporation, after which water was added to the residue and extraction was carried out with ethyl acetate. The ethyl acetate extract was washed with water and dried, and ethyl acetate was removed by evaporation to obtain an oily product. This oily product was column-chromatographed on silica gel to obtain 1.6 g of the desired compound.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux
  3. customreaction
  4. customwas removed by evaporation
  5. additionafter which water was added to the residue and extraction
  6. extractionThe ethyl acetate extract
  7. washwas washed with water
  8. customdried
  9. customethyl acetate was removed by evaporation
  10. customto obtain an oily product
  11. customThis oily product was column-chromatographed on silica gel

Sources & evidence

ORD record
ord-d482f90256b146749dd9e3669144277b
Source dataset
uspto-grants-1989_06
Patent number
US04843068

Reaction notes

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