Hydrochloric Acid → HCID 46180545, compound

HRID 1095437Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[C:10]([CH2:18][CH3:19])=[C:11]([C:13]([O:15]CC)=[O:14])[N:12]=1.[Li+].[OH-].Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:20]2[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=2)[C:10]([CH2:18][CH3:19])=[C:11]([C:13]([OH:15])=[O:14])[N:12]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Part A: Ethyl 2-(2-chlorophenyl)-1-(4-chlorophenyl)-5-ethyl-1H-imidazole-4-carboxylate was obtained according to WO03040107. To a magnetically stirred solution of ethyl 2-(2-chlorophenyl)-1-(4-chlorophenyl)-5-ethyl-1H-imidazole-4-carboxylate (5.80 g, 0.0149 mol) in tetrahydrofuran (40 ml) was added a solution of LiOH (0.715 g) in water (40 ml). The resulting mixture was heated at 70° C. for 16 hours. The resulting mixture was allowed to attain room temperature and subsequently treated with concentrated hydrochloric acid (3.5 ml). The tetrahydrofuran was evaporated in vacuo and the resulting mixture was stirred overnight. The formed precipitate was collected by filtration and washed with petroleum ether (40-60) to give 2-(2-chlorophenyl)-1-(4-chlorophenyl)-5-ethyl-1H-imidazole-4-carboxylic acid (4.52 g, 84% yield). 1H-NMR (400 MHz, CDCl3): δ 1.09 (t, J=7, 3H), 2.90 (q, J=7, 2H), 3.70 (br s, 1H), 7.12 (dtm J=8 and 2, 2H), 7.22-7.28 (m, 1H), 7.29-7.38 (m, 5H).

Workup

customto attain room temperature
customThe tetrahydrofuran was evaporated in vacuo
filtrationThe formed precipitate was collected by filtration
washwashed with petroleum ether (40-60)

Sources & evidence

ORD record: ord-d08e847a416449b19c7a1de8a6d273f6
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138174B2

Reaction notes

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