ChemicalBook CAS DataBase List 5-Acetyl-2,4-dimethylthiazole

5-Acetyl-2,4-dimethylthiazole synthesis

7synthesis methods

Product Name:5-Acetyl-2,4-dimethylthiazole
CAS Number:38205-60-6
Molecular formula:C7H9NOS
Molecular Weight:155.22

62-55-5 Synthesis

62-55-5
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$9.00/5 g

1694-29-7
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$40.00/10 g

38205-60-6
269 suppliers
$6.00/1g

Yield:38205-60-6 78%

Reaction Conditions:

Stage #1:thioacetamide;3-chloropentane-2,4-dione in toluene for 2 h;Reflux;Dean-Stark;Hantzsch Thiazole Synthesis;
Stage #2: with sodium carbonate in chloroform;water at 20;

Steps:

General procedure for the synthesis of thiazolyl ketones 3aa-al
General procedure: To a boiling mixture of the corresponding thioamide 2 (1 eq.) and toluene (ca. 700 mL per 1 mol of 1a), 3-chloropentane-2,4-dione 1a (1.05 eq.) was added dropwise, and the resulting mixture refluxed using Dean-Stark water trap for 2 h. The reaction progress was monitored by measuring the water amount in Dean-Stark trap. When no further water was trapped, the reaction mixture was cooled to r.t. and washed with 10% solution of Na₂CO₃ to adjust the pH of aqueous phase to ca. 7. The organic layer was then washed with brine, dried over Na₂SO₄, filtered and concentrated to 2/3 volume. The extract was purged with dry HCl while stirring at r.t. The formed thiazolyl ketone hydrochloride was filtered off, washed with toluene and hexane, dried under air and recrystallized from EtOH or acetone. The as-obtained hydrochloride was quenched with a mixture of saturated aqueous solution of Na₂CO₃/CHCl₃ (3:1), and the resulting suspension stirred at r.t. until the complete dissolving of the solid. The aqueous phase was separated and extracted with CHCl₃. The combined organic layers were washed with brine, dried over Na₂SO₄, filtered and concentrated under reduced pressure to yield pure target thiazolyl ketones.

References:

Kulyk, Olesia G.;Biloborodov, Dmytro A.;Cherevatenko, Maksim A.;Shyriakin, Yevhen Y.;Lyapunov, Alexander Yu.;Mazepa, Alexander V.;Vashchenko, Valerii V.;Orlov, Valeriy D.;Kolosov, Maksim A. [Synthetic Communications,2020,vol. 50,# 23,p. 3616 - 3628] Location in patent:supporting information

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3043-28-5 Synthesis