Thiobenzamide → HCID 22911939, compound

HRID 1378608Notes

Reaction equation

HRID 1378608 reaction equation
Br[CH:2]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.[C:22]([NH2:30])(=[S:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(#N)C>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:30]=[C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[S:29][C:2]=2[C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 683563ThiobenzamideHCID 112340792-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone

Product 1

HCID 22911939HCID 22911939, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone (Example 26, Step 2) (0.468 g, 1.26 mmol) in acetonitrile (10 mL) in a 25 mL round bottom flask was added thiobenzamide (0.164 g, 1.20 mmol) and the solution heated to reflux (19 hours). The reaction was cooled to room temperature. The resulting suspension was concentrated in vacuo, suspended in methylene chloride (100 mL) and washed with NaHCO3 saturated solution (3×10 mL), dried over sodium sulfate, filtered and concentrated yielding 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-phenylthiazole (0.085 g, 16%) as a fine white powder: mp 188°-189° C., 1HNMR (CDCl3) 300 mHz 8.01 (m, 2H), 7.90 (d, J=8.48 Hz, 2 H), 7.62-7.55 (m, 4 H), 7.55-7.44 (m, 3 H), 7.04 (t, J=8.85 Hz, 2 H), 3.09 (s, 3H); MS (EI-thermospray) m/z 410 (MH+). HRMS (EI) Δ=-2.0 mmu.

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux (19 hours)
  3. concentrationThe resulting suspension was concentrated in vacuo
  4. washwashed with NaHCO3 saturated solution (3×10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ed64580fbdb441b593bc4ac1bde1c03e
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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