Potassium Carbonate → HCID 46908550, compound

HRID 1627244Notes

Reaction equation

HRID 1627244 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:14]2[N:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[C:17](=[S:26])[NH:16][CH:15]=2)([CH3:13])[CH3:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([O-])([O-])=O.[K+].[K+].[Cl:33][C:34]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=1[CH2:41]Cl>CC(C)=O>[Cl:33][C:34]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=1[CH2:41][S:26][C:17]1[N:18]([C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[C:14]([C:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)([CH3:13])[CH3:12])=[CH:15][N:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27250642-Chloro-1-(chloromethyl)-4-fluorobenzeneHCID 68089238HCID 68089238, compound

Product 1

HCID 46908550HCID 46908550, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-(2-(3,4-dimethoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2(3H)-thione (170 mg, 0.46 mmol) and K2CO3 (95 mg, 0.69 mmol) in acetone (5 mL) was stirred for 30 min at room temperature. The resulting mixture was charged with 2-chloro-1-(chloromethyl)-4-fluorobenzene (98 mg, 0.55 mmol) and then heated at reflux overnight. The reaction mixture was cooled to room temperature and filtered through a Celite™ pad. The filtrate was evaporated in vacuo to give a crude product, which was purified by flash chromatography to afford the title product (208 mg, 89%). 1H NMR (400 MHz, CDCl3) δ 7.24 (m, 1H), 7.20 (s, 1H), 7.04 (dd, 1H), 6.86 (td, 1H), 6.74 (m, 2H), 6.64 (d, 1H), 6.45-6.43 (m, 2H), 6.21 (m, 2H), 4.25 (s, 2H), 3.86 (s, 3H), 3.71 (s, 3H), 1.47 (s, 6H); MS (EI) m/z 515 (MH+).

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered through a Celite™ pad
  5. customThe filtrate was evaporated in vacuo
  6. customto give a crude product, which
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-e870c4eb0ed4452f8429c2c60ceb5c43
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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