Dichloromethane → HCID 54412494, compound

HRID 1378580Notes

Reaction equation

HRID 1378580 reaction equation
Br[CH:2]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=O.[C:20]([NH2:23])(=[S:22])[CH3:21].C(Cl)Cl.CCCCCC>C(O)C>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:2]2[S:22][C:20]([CH3:21])=[N:23][C:3]=2[C:5]2[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8058HexaneHCID 2723949ThioacetamideHCID 54373829HCID 54373829, compound

Product 1

HCID 54412494HCID 54412494, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-bromo-2-(4-fluorophenyl)-1-(4-methylthiophenyl) ethanone from Step 2 (0.70 g, 2.10 mmol) in ethanol (20 mL) in a 50 mL round bottom flask was added thioacetamide (0.16 g, 2.10 mmol) and the mixture heated to reflux for 20 hours. The reaction was cooled to room temperature and concentrated in vacuo and dissolved in methylene chloride. This solution was washed with NaHCO3 saturated solution and dried over Na2SO4, filtered and reconcentrated in vacuo yielding a white crystalline solid. Flash chromatography of this solid (2:1 methylene chloride: hexane) yielded 5-(4-fluorophenyl)-4-(4-methylthiophenyl) -2-methylthiazole as a white solid (0.45 g, 68%): mp 104°-105° C. 1H NMR (CDCl3) 400 mHz δ7.39 (d, J=8.32, 2H), 7.28 (dd, J=8.80, 5.14, 2H), 7.15 (d, J=8.32, 2H), 7.00 (t, J=8.80, 2H), 2.74 (s, 3H), 2.47 (s, 3H). MS (EI): m/z 316 (M+H). HRMS Δ=0.000 mmu.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 20 hours
  3. concentrationconcentrated in vacuo
  4. dissolutiondissolved in methylene chloride
  5. washThis solution was washed with NaHCO3 saturated solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customyielding a white crystalline solid

Sources & evidence

ORD record
ord-b77f595f1e0f4677a732f530a2e27cf2
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

Loading…