ChemicalBook CAS DataBase List 2-MERCAPTO-4(3H)-QUINAZOLINONE

2-MERCAPTO-4(3H)-QUINAZOLINONE synthesis

12synthesis methods

Product Name:2-MERCAPTO-4(3H)-QUINAZOLINONE
CAS Number:13906-09-7
Molecular formula:C8H6N2OS
Molecular Weight:178.21

16024-82-1
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13906-09-7
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$45.00/250mg

Yield: 96%

Reaction Conditions:

with pyridine;ammonia in toluene at -34 - 20; under 1500.15 Torr; for 1 h;Inert atmosphere;Sealed tube;

Steps:

2-Thioxo-2,3-dihydroquinazolin-4(1H)-one (9a)
A solution of methyl 2-isothiocyanatobenzoate (8a)(2.15 g, 11.16 mmol) in dry toluene (10 mL) and pyridine (1.35 mL, 16.74 mmol) was placed in a 15 mL pressure tube (reactor) under argon atmosphere. After the solution was cooled to -34 C, ammonium gas was added in excess at a rate that kept the solution below -34 C. The tube was carefully sealed, and the solution was stirred at rt for 1 h (pressure 2 bar). The white precipitate obtained was collected by filtration,washed with toluene, and recrystallized from MeOH to afford compound 9a (1.91 g, 96%) as white needles; mp 296-297 C (lit.37 mp 300 C).

References:

Kri??iūnien?, Vilija;Matulevi?iūt?, Gita;Paliulis, Osvaldas;Rollin, Patrick;?a?kus, Algirdas [Heterocycles,2016,vol. 93,# 1,p. 150 - 163]