Hydrochloric Acid → 5-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylic acid

HRID 2067582Notes

Reaction equation

[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:11](=[O:12])[N:10]([C:13]3[S:17][C:16]([C:18]([O:20]CC)=[O:19])=[C:15]([CH3:23])[CH:14]=3)[CH:9]=[N:8]2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(O)C>[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:11](=[O:12])[N:10]([C:13]3[S:17][C:16]([C:18]([OH:20])=[O:19])=[C:15]([CH3:23])[CH:14]=3)[CH:9]=[N:8]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of ethyl 5-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylate (0.17 g, 0.47 mmol) and 1 N aqueous sodium hydroxide solution (3.0 mL, 3.0 mmol) in ethanol (6 mL) was stirred at reflux for 1 h, cooled to 0° C. and acidified with 10% aqueous hydrochloric acid to pH ˜2. The resulting precipitate was filtered, washed with water and hexanes, and dried in vacuo to afford the title compound as a colorless solid in 82% yield (0.13 g): 1H NMR (300 MHz, DMSO-d6) δ 12.94 (br s, 1H), 8.70 (s, 1H), 7.36-7.29 (m, 2H), 7.23 (s, 1H), 7.19-7.11 (m, 2H), 4.92 (s, 2H), 2.43 (s, 3H); MS (ES−) m/z 332.1 (M−1).

Workup

temperatureat reflux for 1 h
filtrationThe resulting precipitate was filtered
washwashed with water and hexanes
customdried in vacuo

Sources & evidence

ORD record: ord-ff3e65f1fe804e2985cbe4b870e0253c
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293768B2

Reaction notes

Loading…