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

HRID 560875Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of ethyl 3-methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylate (0.09 g, 0.24 mmol) and 1 N aqueous sodium hydroxide solution (1.5 mL, 1.5 mmol) in ethanol (3 mL) was stirred at reflux for 1 h, and then cooled to 0° C. and acidified with 10% aqueous hydrochloric acid to pH ˜2. The aqueous layer was extracted with dichloromethane (2×50 mL), and the combined organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a colorless solid in 99% yield (0.08 g): 1H NMR (300 MHz, DMSO-d6) δ 12.33 (br s, 1H), 7.29 (dd, J=8.8, 7.2 Hz, 2H), 6.99-6.93 (m, 3H), 6.28 (s, 1 H), 4.13 (t, J=5.3 Hz, 2H), 3.87-3.79 (m, 2H), 3.72-3.64 (m, 2H), 3.58 (t, J=5.3 Hz, 2 H), 2.39 (s, 3H): MS (ES+) m/z 347.3 (M+1).

Workup

temperatureat reflux for 1 h
extractionThe aqueous layer was extracted with dichloromethane (2×50 mL)
dry with materialthe combined organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8ac7393c5e8148e0aede28ae82121342
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063084B2

Reaction notes

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