desmethylanethol trithione

Anethole (1) (32.5 g; 0.21 mol) and sulphur (45 g; 1.40 mol) were heated in dimethylformamide (250 ml) for 8 hr; the residue after removal of solvent was almost completely soluble in toluene. An attempt to extract the toluene liquors with 2N-aqueous sodium hydroxide, gave a precipitate of an orange solid (8.5 g). m.p. over 300° C. This product was dissolved in boiling water and gave an orange precipitate (2) after addition of hydrochloric acid (Yield 50percent), m.p. 188-189° C. EXAMPLE 3General synthetic procedure of:4- or 5-Amino-2-hydroxy-benzoic acid 4-(5-thioxo-5H-[1, 2]dithiol-3-yl)-phenyl ester(4)4- or 5-nmlno salicylic acidSynthesis of5-p-hydroxyphenyl-1, 2-dithione-3-thione (ADT-OH)Anethole 1 (32.5 g; 0.21 mol) and sulphur (45 g; 1.40 mol) were heated in dimethylformamide (250 ml) for 8 hr; the residue after removal of solvent was almost completely soluble in toluene. An attempt to extract the toluene liquors with 2N- aqueous sodium hydroxide, gave a precipitate of an orange solid (8.5 g). m.p. over 300EXAMPLE 3General synthetic procedure of:4- or 5-Amino-2-hydroxy-benzoic acid 4-(5-thioxo-5H-[1, 2]dithiol-3-yl)-phenyl ester(4)4- or 5-nmlno salicylic acidSynthesis of5-p-hydroxyphenyl-1, 2-dithione-3-thione (ADT-OH)Anethole 1 (32.5 g; 0.21 mol) and sulphur (45 g; 1.40 mol) were heated in dimethylformamide (250 ml) for 8 hr; the residue after removal of solvent was almost completely soluble in toluene. An attempt to extract the toluene liquors with 2N- aqueous sodium hydroxide, gave a precipitate of an orange solid (8.5 g). m.p. over 300Synthesis of 5-p-hydroxyphenyl-1, 2-dithiole-3-thione (2; ADT-OH) ADT-OMe (2.00 g, 8.32 mmol), and anhydrous pyridine hydrochloride (5.77 g, 49.9 mmol) were added to an oven-dried pressurevessel under N2. The apparatus was submerged into an oil bath and stirred at 220 °C. Afterstirring for 25 minutes, the reaction flask was cooled to room temperature, and the contents weredissolved in methanol and transferred to a round bottom flask. The methanol was removed, andthe contents of the round bottom were dissolved in a 50:50 mixture of 0.5 M HCl and EtOAc inorder to solubilize the crude product. This mixture was then further diluted with water andextracted into EtOAc. The organic layer was dried with Na2SO4 and purified by columnchromatography (3:2 Hex:EtOAc) to afford ADT-OH as a lovely golden orange solid (1.60 g, 85percent).A mixture of ATT 1 (10.05 g, 40 mmol) and anhydrous pyridine hydrochloride (34.07 g, 290 mmol) was heated to 220 °C for 20 min under argon atmosphere. The system was cooled to room temperature, and then 100 ml water was poured in and stirred for 5 min. The suspension was filtered, and the filter cake was collected. The solid was dissolved in 100 ml of 10percent NaOH aqueous solution and stirred for 10 min, then filtered, the filtrate was acidified to pH 1 by conc HCl to form massive solid, then filtered and the filtter cake was dried in vacuo to afford 2 as orange solid (7.65g, 84.5percent).Compound 1 (200 mg, 1.0 eq.) and pyridine hydrochloride (577 mg, 6.0 eq) were added to a 10 mL microwave reaction vessel. The reaction conditions were as follows: temperature: 200°C, power: 200 Watt, ramp time: 1 min, hold time: 6 min. After cooling, the reaction mixture was dissolved in a mixture of CHDry anethol sulfur (6.0185 g)With anhydrous pyridine hydrochloride (30.1553 g)In a dry crystallized 250 ml three-necked round bottom flask, The oil bath was heated to 220 ° C, the solid melted and the reaction started.The reaction is terminated in 60 min.Cool to room temperature, add 1M / L dilute HCl to dissolve and filter. The filtrate was discarded, washed with distilled water until neutral and filtered.Finally, the product was recrystallized from absolute ethanol (2.9444g).Yield: 49percentGeneral synthetic procedure of: 4- or 5-Amino-2-hydroxy-benzoic acid 4-(5-thioxo-5H-[1, 2]dithiol-3-yl)-phenyl ester (4) [Compound of Formula XXXV]; Synthesis of 5-p-hydroxyphenyl-1, 2-dithione-3-thione (ADT-OH); Anethole (1) (32.5 g; 0.21 mol) and sulphur (45 g; 1.40 mol) were heated in dimethylformamide (250 ml) for 8 hr; the residue after removal of solvent was almost completely soluble in toluene. An attempt to extract the toluene liquors with 2N-aqueous sodium hydroxide, gave a precipitate of an orange solid (8.5 g). m.p. over 300° C. This product was dissolved in boiling water and gave an orange precipitate (2) after addition of hydrochloric acid (Yield 50percent), m.p. 188-189° C.

Molecular Weight:226.3
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:225.95807833
Monoisotopic Mass:225.95807833
Topological Polar Surface Area:103
Heavy Atom Count:13
Complexity:241
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes