Hydrochloric Acid → 3-Methyl-5-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiophene-2-carboxylic acid

HRID 560707Notes

Reaction equation

[CH3:1][C:2]1[CH:6]=[C:5]([N:7]2[CH2:11][CH2:10][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[C:8]2=[O:23])[S:4][C:3]=1[C:24]([O:26]CC)=[O:25].[OH-].[Na+].Cl>C(O)C>[CH3:1][C:2]1[CH:6]=[C:5]([N:7]2[CH2:11][CH2:10][N:9]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:17][CH:18]=3)[C:8]2=[O:23])[S:4][C:3]=1[C:24]([OH:26])=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of ethyl 3-methyl-5-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiophene-2-carboxylate (4.31 g, 10.5 mmol) and 1 N aqueous sodium hydroxide solution (60 mL, 60 mmol) in ethanol (120 mL) was stirred at reflux for 1.5 h, then cooled to 0° C. and acidified with 10% aqueous hydrochloric acid to pH ˜2. The white precipitate was filtered, washed with water and ethanol, and then dried in vacuo to afford the title compound as a colorless solid in 91% yield (3.68 g): 1H NMR (300 MHz, DMSO-d6) δ 12.37 (br s, 1H), 7.74 (d, J=8.1 Hz, 2H), 7.53 (d, J=8.1 Hz, 2 H), 6.30 (s, 1H), 4.50 (s, 2H), 3.90-3.81 (m, 2H), 3.52-3.44 (m, 2H), 2.40 (s, 3H): MS (ES+) m/z 385.2 (M+1).

Workup

temperatureat reflux for 1.5 h
filtrationThe white precipitate was filtered
washwashed with water and ethanol
customdried in vacuo

Sources & evidence

ORD record: ord-745123aaad97412ca47cbf90ba07d306
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063084B2

Reaction notes

Loading…