4-Methoxybenzenecarbothioamide → HCID 22911832, compound

HRID 1378612Notes

Reaction equation

HRID 1378612 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.[CH3:22][O:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH2:30])=[S:29])=[CH:26][CH:25]=1>C(O)(C)C>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:30]=[C:28]([C:27]3[CH:31]=[CH:32][C:24]([O:23][CH3:22])=[CH:25][CH:26]=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 7368274-MethoxybenzenecarbothioamideHCID 112340792-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone

Product 1

HCID 22911832HCID 22911832, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 2-bromo-1- (4-fluorophenyl) -2- (4-methylsulfonylphenyl) ethanone (Example 26, Step 2) (0.500 g, 1.35 mmol) in isopropanol (10 mL) in a 25 mL round bottom flask was added p-methoxythiobenzamide (0.230 g, 1.35 mmol). The solution was heated to reflux for 30 hours and 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-(4-methoxyphenyl)thiazole (0.360 g, 61%) as a crystalline solid: mp 187°-189° C., 1HNMR (CDCl3) 300 mHz 7.99 (d, 8.82 Hz, 2 H), 7.93 (d, J=8.50 Hz, 2 H), 7.63-7.53 (m, 4 H), 7.09 (t, J=8.63 Hz, 2 H), 7.03 (d, J=8.82 Hz, 2 H), 3.92 (s, 3 H), 3.13 (s, 3 H); MS m/z 440 (M+H). HRMS Δ=2.0 mmu.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 30 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-7c4dda28c239471f9c0f76e9817688f1
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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