Hydrochloric Acid → 3-[5-(4-Cyano-phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-benzoic acid
Reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]2[O:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=3)=[N:14][N:15]=2)[CH:5]=1.O.[OH-].[Na+].Cl>CO>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([C:13]2[O:12][C:11]([CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:24])=[O:2])=[N:15][N:14]=2)=[CH:21][CH:20]=1)#[N:23]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Suspend of 3-[5-(4-cyano-phenyl)[1,3,4]oxadiazol-2-ylmethyl]-benzoic acid methyl ester (0.120 g, 0.376 mmol) in 4 mL of a 1:1 mixture of H2O:MeOH. Heat the mixture to 60° C., and add 10% aqueous solution of NaOH (0.28 mL, 0.70 mmol). Stir at 60° C. for 30 minutes, cool to room temperature and adjust the pH to 5 by the addition of a 2 N solution of HCl. Concentrate the mixture overnight under a stream of air, dilute crude residue with H2O and extract with methylene chloride. Wash the combined organic phase with brine, dry over anhydrous sodium sulfate and concentrate to provide 0.11 g 4% yield of 3-[5-(4-cyano-phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-benzoic acid as a white solid.
Workup
- temperaturecool to room temperature
- concentrationConcentrate the mixture overnight under a stream of air
- additiondilute crude residue with H2O
- extractionextract with methylene chloride
- washWash the combined organic phase with brine
- dry with materialdry over anhydrous sodium sulfate
- concentrationconcentrate
Sources & evidence
- ORD record
- ord-f728190464cc4ef4971645728d7ffdb6
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09000154B2
Reaction notes
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