Ethylene Glycol → HCID 58243619, compound

HRID 389132Notes

Reaction equation

HRID 389132 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]([CH3:27])[C:11]([C:14]([CH3:26])([O:16][C:17]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:18]=2[C:19]#N)[CH3:15])=[N:12][N:13]=1.[OH-:28].[Na+].[OH2:30].[CH2:31]([OH:34])[CH2:32][OH:33]>>[Br:1][C:2]1[CH:7]=[C:6]([O:33][CH2:32][CH2:31][OH:34])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]([CH3:27])[C:11]([C:14]([CH3:15])([O:16][C:17]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:18]=2[C:19]([OH:30])=[O:28])[CH3:26])=[N:12][N:13]=1

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 14798Sodium HydroxideHCID 58243658HCID 58243658, compound

Product 1

HCID 58243619HCID 58243619, compound

Conditions

Temperature
130 °C

Procedure

2-{1-[5-(2-bromo-4-fluorophenyl)-4-methyl-4H-1,2,4-triazol-3-yl]-1-methylethoxy}-5-chloro-benzonitrile (1.93 g) was suspended in ethyleneglycol (20 ml), and a 5M aqueous sodium hydroxide solution (4.3 ml) was added thereto, followed by stirring at 130° C. for 24 hours. The reaction solution was cooled to room temperature, and water was added thereto, followed by washing with ethyl acetate. The aqueous layer was acidified with 1M hydrochloric acid and extracted with ethyl acetate. 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 2-(1-{5-[2-bromo-4-(2-hydroxyethoxy)phenyl]-4-methyl-4H-1,2,4-triazol-3-yl}-1-methylethoxy)-5-chlorobenzoic acid (1.77 g) as a beige solid.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. washby washing with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. washThe resulting solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-b3189917769e4f9ca2e6efdbaee93225
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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