ChemicalBook CAS DataBase List thiazol-3-one

thiazol-3-one synthesis

3synthesis methods

Product Name:thiazol-3-one
CAS Number:1003-07-2
Molecular formula:C3H3NOS
Molecular Weight:101.13

1668-10-6 Synthesis

1668-10-6
473 suppliers
$5.00/5g

1003-07-2
107 suppliers
$35.00/100mg

Yield: 90%

Reaction Conditions:

with sulfuryl dichloride in DMF (N,N-dimethyl-formamide) at 5 - 15; for 7.5 h;

Steps:

76 Method 76; 3-Oxo-2,3-dihydroisothiazole
Glycinamide.HCl (1 mol) was suspended in DMF (500 ml) and SO₂Cl₂ (300 ml) was added dropwise over 1.5 hours with cooling keeping the reaction temperature between 5-10° C. The reaction was stirred at 10-15° C. for 6 hours when water (500 ml) was added cautiously. The solid was removed by filtration and the filtrate extracted with ether (21). The Ethereal solution was washed brine (200 ml) and evaporated in vacuo to yield a pale yellow solid (132 g)-A. The aqueous layer was extracted with DCM (2*600 ml). The DCM portions were combined and washed with ether and water. The organic layer was washed brine and evaporated in vacuo to yield a cream solid (18 g)-B. A & BD were combined, dissolved in ether, dried and charcoal was added. The solution was filtered and the filtrate evaporated in vacuo to yield a pale yellow solid (104.3 g). This solid was triturated with isohexane to yield the title compound (91.3 g, 90%). Mpt: 102-5° C.

References:

Breault, Gloria Anne;Newcombe, Nicholas John;Thomas, Andrew Peter US2004/14776, 2004, A1 Location in patent:Page/Page column 37-38