Hexane → Thiazole, 2-methyl-4-(2-phenylethynyl)-

HRID 967741Notes

Reaction equation

HRID 967741 reaction equation
Cl[CH2:2][C:3](=O)[C:4]#[C:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:13]([NH2:16])(=[S:15])[CH3:14].CCCCCC.C(OCC)(=O)C>C(#N)C>[CH3:14][C:13]1[S:15][CH:2]=[C:3]([C:4]#[C:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:16]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 2723949ThioacetamideHCID 110085031-chloro-4-phenyl-3-Butyn-2-one

Product 1

HCID 10921526Thiazole, 2-methyl-4-(2-phenylethynyl)-Yield 13.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Chloro-4-phenyl-3-butyn-2-one (1.6 g, 9.1 mmol) was dissolved in dry acetonitrile (15 mL), treated with thioacetamide (680 mg, 9.1 mmol), and heated to reflux for 4 h. After cooling, the acetonitrile was removed in vacuo, and the residue was partitioned between water (50 mL) and ethyl acetate (150 mL). The organic phase was dried over Na2SO4, filtered, concentrated in vacuo, adsorbed onto silica gel, and purified by column chromatography on silica gel eluting with 99:1, 98:2, then 95:5 hexane:ethyl acetate to afford 2-methyl-4-(phenylethynyl)-1,3-thiazole (240 mg, 13% yield) as a red oil. 1H NMR (CDCl3, 300 MHz) δ 7.58–7.54 (m, 2H), 7.40–7.34 (m, 4H), 2.74 (s, 3H). MS (EI ionization) 199 (M+).

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 h
  3. temperatureAfter cooling
  4. customthe acetonitrile was removed in vacuo
  5. customthe residue was partitioned between water (50 mL) and ethyl acetate (150 mL)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. custompurified by column chromatography on silica gel eluting with 99:1, 98:2

Sources & evidence

ORD record
ord-232790385440430ea6afc1e992f5db17
Source dataset
uspto-grants-2005_10
Patent number
US06956049B1

Reaction notes

Loading…