Potassium Carbonate → 2-(2-chloro-6-fluorobenzylthio)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole

HRID 1627246Notes

Reaction equation

HRID 1627246 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:15](=[S:24])[NH:14][CH:13]=2)([CH3:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8].C([O-])([O-])=O.[K+].[K+].[Cl:31][C:32]1[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[C:33]=1[CH2:34]Cl>CC(C)=O>[Cl:31][C:32]1[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[C:33]=1[CH2:34][S:24][C:15]1[N:16]([C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)[C:12]([C:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)([CH3:11])[CH3:10])=[CH:13][N:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1086751-Chloro-2-(chloromethyl)-3-fluorobenzeneHCID 667403425-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol

Product 1

HCID 469086492-(2-chloro-6-fluorobenzylthio)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazoleYield 40.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2(3H)-thione (138 mg, 0.362 mmol) and K2CO3 (76 mg, 0.543 mmol) in acetone (6 mL) was added 2-chloro-6-fluorobenzyl chloride (79 mg, 0.434 mmol). After stirring 2 h, the reaction mixture was filtered, concentrated and purified by flash chromatography to provide the title product (77 mg, 33%). 1H NMR (400 MHz, CDCl3) δ 7.25 (m, 1H), 7.22 (s, 1H), 7.16-7.11 (m, 2H), 7.03 (d, 1H), 6.91 (m, 1H), 6.83 (dd, 1H), 6.78 (t, 2H), 6.34 (m, 2H), 4.25 (s, 2H), 1.49 (s, 6H); MS (EI) m/z 523, 525 (MH+).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-991e72825b7f44859742e76a628bf901
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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