Water → HCID 18408345, compound

HRID 1385961Notes

Reaction equation

HRID 1385961 reaction equation
[NH2:1][C:2]1[C:3]([OH:21])=[CH:4][C:5]([Cl:20])=[C:6]([C:8]2[C:9](=[O:19])[N:10]([CH3:18])[C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=2)[CH:7]=1.C1N=CN([C:27](N2C=NC=C2)=[O:28])C=1.O>C1COCC1>[Cl:20][C:5]1[C:6]([C:8]2[C:9](=[O:19])[N:10]([CH3:18])[C:11]([C:14]([F:17])([F:15])[F:16])=[CH:12][CH:13]=2)=[CH:7][C:2]2[NH:1][C:27](=[O:28])[O:21][C:3]=2[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 15457077HCID 15457077, compound

Product 1

HCID 18408345HCID 18408345, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.6 g (1.9 mmol) of 3-(5-amino-2-chloro-4-hydroxyphenyl)-1-methyl-6-trifluoromethyl-2(1H)-pyridone and 0.35 g (2.2 mmol) of CDI were dissolved in 5 ml of THF, followed by stirring for 1 hour under heating and refluxing. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The organic layer was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.41 g (yield: 63%) of the desired product. Melting point: 263-265° C. 1H-NMR (400 MHz, CDCl3) δ value: 3.78(3H,s), 6.84(1H,s), 6.85(1H,d), 7.28(1H,s), 7.46(1H,d)ppm.

Workup

  1. temperatureunder heating
  2. temperaturerefluxing
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe organic layer was distilled off under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-09be6f84c3b54df2897929e6c3cacfa8
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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