Hydrochloric Acid → 3-[5-(4-Cyano-phenyl)-[1,3,4]thiadiazol-2-ylmethyl]-benzoic acid

HRID 1468170Notes

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[S: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.CO.[OH-].[Na+].Cl>O.C1COCC1>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([C:13]2[S: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

Conditions

Temperature: 60 °C

Procedure

Suspend 3-[5-(4-cyano-phenyl)-[1,3,4]thiadiazol-2-ylmethyl]-benzoic acid methyl ester (0.15 g, 0.45 mmol) in 10 mL of a 1:1 mixture of H2O:MeOH, add 10% aqueous solution of NaOH (0.48 mL, 1.20 mmol) and heat to 60° C. After stifling for 3 h add 5 mL of THF to the reaction mixture causing all of the solids to go into solution. Heat the mixture at 60° C. for an additional 2 h then cool to room temperature. Adjust the pH to slightly acidic by the addition of a 2N solution of HCl. Dilute the mixture with H2O and wash with CH2Cl2. Wash the combined organics with brine, dry over anhydrous sodium sulfate and concentrate to provide 0.13 g, 57% yield of 3-[5-(4-cyano-phenyl)-[1,3,4]thiadiazol-2-ylmethyl]-benzoic acid as a solid.

Workup

temperatureHeat the mixture at 60° C. for an additional 2 h
temperaturethen cool to room temperature
washwash with CH2Cl2
washWash the combined organics with brine
dry with materialdry over anhydrous sodium sulfate
concentrationconcentrate

Sources & evidence

ORD record: ord-e17ed9f6d10146079cab0b7be3f9fb93
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000154B2

Reaction notes

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