Thioacetamide → 4-(4-Fluorophenyl)-5-(4-methylsulfonylphenyl)-2-methylthiazole

HRID 1378587Notes

Reaction equation

HRID 1378587 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]([NH2:25])(=[S:24])[CH3:23]>C(#N)C>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:25]=[C:22]([CH3:23])[S:24][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 2723949ThioacetamideHCID 112340792-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone

Product 1

HCID 101722374-(4-Fluorophenyl)-5-(4-methylsulfonylphenyl)-2-methylthiazoleYield 55.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone (0.437 g, 1.18 mmol) (Example 26, Step 2) in acetonitrile (10 mL) in a 25 mL round bottom flask was added thioacetamide (0.088 g, 1.18 mmol) and the solution heated to reflux (2 hours) until all solid dissolved. The reaction was cooled to room temperature. The acetonitrile was removed in vacuo and the resulting product precipitated from methanol by the addition of water yielding 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-methylthiazole (0.226 g, 55%, ca. 85% purity by 1H NMR): mp 229°-233° C. 1HNMR (CDCl3) 300 mHz δ7.98 (d, J=8.11 Hz, 2H ), 7.66-7.61 (m, 2H), 7.52 (d, J=8.48 Hz, 2H), 7.13 (t, J=8.48 Hz, 2H), 3.31 (s, 1H), 3.10 (s, 3H). MS (EI-thermospray): m/z 348 (M+). HRMS Δ=-2.3 mmu.

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux (2 hours) until all solid
  3. dissolutiondissolved
  4. customThe acetonitrile was removed in vacuo
  5. customthe resulting product precipitated from methanol by the addition of water

Sources & evidence

ORD record
ord-92606651d5024c4b9c838d42172facf9
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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