Sodium Hydroxide → HCID 22228199, compound

HRID 1744586Notes

Reaction equation

HRID 1744586 reaction equation
C([CH:3]([C:37]([OH:39])=[O:38])[N:4]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[C:25]([C:35]#[N:36])[CH:24]=1)[C:5]([C:7]1[C:8]([CH3:22])=[N:9][N:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[CH:11]=1)=[O:6])C.[OH-].[Na+]>C(O)C>[C:35]([C:25]1[CH:24]=[C:23]([N:4]([C:5]([C:7]2[C:8]([CH3:22])=[N:9][N:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:21])[F:19])[CH:13]=3)[CH:11]=2)=[O:6])[CH2:3][C:37]([OH:39])=[O:38])[CH:28]=[CH:27][C:26]=1[O:29][CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])#[N:36]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22228007HCID 22228007, compound

Product 1

HCID 22228199HCID 22228199, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl N-(3-cyano-4-neopentyloxyphenyl)-N-[1-(3-trifluoromethylphenyl)-3-methylpyrazol-4-ylcarbonyl]glycine (1.5 g) was added to ethanol (15 ml). 10% Aqueous sodium hydroxide solution (10 ml) was added and the mixture was stirred at a refluxing temperature for 30 min. The solvent was evaporated under reduced pressure. Dilute hydrochloric acid was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. A mixed solvent of chloroform-n-hexane was added to the residue to allow crystallization. The crystals were recrystallized from hydrous acetic acid to give the title compound (0.9 g), melting point: 110–112° C.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionDilute hydrochloric acid was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customafter which the solvent was evaporated under reduced pressure
  7. additionA mixed solvent of chloroform-n-hexane was added to the residue
  8. customcrystallization
  9. customThe crystals were recrystallized from hydrous acetic acid

Sources & evidence

ORD record
ord-de70ccd21c6c4b60869585fce9647b8c
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

Loading…