Ethanol → 5-Biphenyl-4-yl-6-fluoro-1,3-dihydro-benzoimidazole-2-thione

HRID 1960132Notes

Reaction equation

CCO.[OH-].[K+].[F:6][C:7]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)=[CH:11][C:10]([NH2:25])=[C:9]([NH2:26])[CH:8]=1.[C:27](=S)=[S:28]>C(O)(=O)C.O>[C:16]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:15]=[CH:14][C:13]([C:12]2[C:7]([F:6])=[CH:8][C:9]3[NH:26][C:27](=[S:28])[NH:25][C:10]=3[CH:11]=2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of EtOH (20 mL), H2O (4 mL) and KOH (593 mg, 11 mmol) was added compound 13-3 (2.46 g, 8.8 mmol). CS2 (0.65 mL, 11 mmol) was then added and the suspension was heated to reflux for 2 h. The reaction mixture was cooled to 25° C., then 40 mL of H2O and 0.8 mL of acetic acid were added resulting in a tan precipitate. The precipitate was collected by vacuum filtration resulting in title compound 13-4, which required no further purification.

Workup

temperaturethe suspension was heated
temperatureto reflux for 2 h
customresulting in a tan precipitate
filtrationThe precipitate was collected by vacuum filtration

Sources & evidence

ORD record: ord-3dba3664ddc948c79fe92be5c813e4bc
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410284B2

Reaction notes

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