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

HRID 1945314
Notes
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Reaction equation

HRID 1945314 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 702EthanolHCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 674456646-Fluoro-[1,1';4'1'']terphenyl-3,4-diamine

Product 1

HCID 866405075-Biphenyl-4-yl-6-fluoro-1,3-dihydro-benzoimidazole-2-thione

Reagents, catalysts & solvents 2

HCID 176
Acetic Acid
Solvent
HCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of EtOH (20 mL), H2O (4 mL) and KOH (593 mg, 11 mmol) was added 4 (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 filtation resulting in title compound 5, which required no further purification.

Workup

  1. temperaturethe suspension was heated
  2. temperatureto reflux for 2 h
  3. customresulting in a tan precipitate
  4. customThe precipitate was collected by vacuum filtation

Sources & evidence

ORD record
ord-a565cab164f04d4bb8f5f175dabe5bd7
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08394969B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes