Ethylene Glycol → HCID 58244041, compound

HRID 389122Notes

Reaction equation

HRID 389122 reaction equation
[OH-:1].[Na+].[ClH:3].Cl[C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[C:13]1[N:17]([CH3:18])[C:16]([C:19]([CH3:31])([O:21][C:22]2[C:27]([F:28])=[CH:26][C:25]([F:29])=[CH:24][C:23]=2[F:30])[CH3:20])=[N:15][N:14]=1)[C:8]#N.C(O)C[OH:34]>O>[Cl:3][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[C:13]1[N:17]([CH3:18])[C:16]([C:19]([CH3:31])([O:21][C:22]2[C:27]([F:28])=[CH:26][C:25]([F:29])=[CH:24][C:23]=2[F:30])[CH3:20])=[N:15][N:14]=1)[C:8]([OH:34])=[O:1]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 67024426HCID 67024426, compound

Product 1

HCID 58244041HCID 58244041, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A 5M aqueous sodium hydroxide solution (3.5 ml) was added to a mixture of 3-chloro-4-{4-methyl-5-[1-methyl-1-(2,4,6-trifluorophenoxy)ethyl]-4H-1,2,4-triazol-3-yl}benzonitrile monohydrochloride (760 mg) and ethyleneglycol (10 ml), followed by stirring at 130° C. for one hour. The reaction solution was cooled to room temperature and water was added thereto, followed by washing with ethyl acetate. 1M hydrochloric acid was added to the organic layer, followed by extraction with a mixed solvent of chloroform and isopropanol (4:1). The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The resulting solid was washed with ethyl acetate to obtain 3-chloro-4-{4-methyl-5-[1-methyl-1-(2,4,6-trifluorophenoxy)ethyl]-4H-1,2,4-triazol-3-yl}benzoic acid (445 mg), as a white solid.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. washby washing with ethyl acetate
  3. addition1M hydrochloric acid was added to the organic layer
  4. extractionfollowed by extraction with a mixed solvent of chloroform and isopropanol (4:1)
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. washThe resulting solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-c7abe3f97e7a4da5a44992c8c3973120
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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