Thionyl Chloride → 4-Chloromethyl-2-ethyl-5-methyl-1,3-thiazole

HRID 2221703Notes

Reaction equation

HRID 2221703 reaction equation
[CH2:1]([C:3]1[S:4][C:5]([CH3:10])=[C:6]([CH2:8]O)[N:7]=1)[CH3:2].S(Cl)([Cl:13])=O>C1(C)C=CC=CC=1>[Cl:13][CH2:8][C:6]1[N:7]=[C:3]([CH2:1][CH3:2])[S:4][C:5]=1[CH3:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23076454(2-Ethyl-5-methyl-1,3-thiazol-4-YL)methanol

Product 1

HCID 230764064-Chloromethyl-2-ethyl-5-methyl-1,3-thiazoleYield 84.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (2-ethyl-5-methyl-1,3-thiazol-4-yl)methanol (3.7 g) in toluene (200 mL) was added thionyl chloride (8.5 g) at room temperature, and the mixture was heated under reflux for 30 min. The solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate was added to the residue and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (10:90-25:75, v/v) to give 4-chloromethyl-2-ethyl-5-methyl-1,3-thiazole as a yellow oil (3.5 g, yield 84%). NMR (CDCl3) δ: 1.35 (3H, t, J=7.6 Hz), 2.44 (3H, s), 2.95 (2H, q, J=7.6 Hz), 4.63 (2H, s).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 min
  3. customThe solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate
  4. additionwas added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. washeluted with ethyl acetate-hexane (10:90-25:75

Sources & evidence

ORD record
ord-8e4d75ab1254429296b912c439a263f6
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

Loading…