Hydrochloric Acid → HCID 58244209, compound

HRID 389127Notes

Reaction equation

HRID 389127 reaction equation
[CH3:1][C:2]([C:21]1[N:25]([CH3:26])[C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]([F:36])([F:35])[F:34])=[N:23][N:22]=1)([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]([O:18]CC)=[O:17])[N:12]=2)=[CH:7][CH:6]=1)[CH3:3].[OH-].[Na+].O.Cl>C(O)C>[CH3:3][C:2]([C:21]1[N:25]([CH3:26])[C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]([F:36])([F:35])[F:34])=[N:23][N:22]=1)([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]([OH:18])=[O:17])[N:12]=2)=[CH:7][CH:6]=1)[CH3:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 58243841HCID 58243841, compound

Product 1

HCID 58244209HCID 58244209, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 5-[4-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)phenyl]-1,2,4-oxadiazole-3-carboxylate (251 mg) was suspended in ethanol (5 ml) and a 1M aqueous sodium hydroxide solution (1 ml) was added thereto, followed by stirring for 5 minutes. Water and 1M hydrochloric acid were added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting solid was washed with ethyl acetate to obtain 5-[4-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)phenyl]-1,2,4-oxadiazole-3-carboxylic acid (207 mg), as a white solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washThe resulting solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-8c5140141d7b49a39047cf4c88c2a3d1
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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