Modafinil acid

Off-White to Pale Pink Solid

Modafinil acid is a diarylmethane.

Preparation of 2-[(Diphenylmethyl)sulfinyl] acetic acid; 2-[(Diphenylmethyl)thio] acetic acid (416 g, 1.61 mol) was suspended in purified water(4160 ml) at 25 to 30Preparation of 2-[(DiphenyImethyI)sulfinyl] acetic acid; 2-[(Diphenylmethyl) thio] acetic acid (5 g) was dissolved in toluene: methanol (10:1, 55 ml) at 25 to 30Preparation of 2-[(DiphenylmethyI)sulfinyl] acetic acid; 2-[(Diphenylmethyl) thio] acetic acid (10 g) was dissolved in methanol (50 ml) at 25 to 3OPreparation of 2-[(Diphenylmethyl)sulfmyl] acetic acid; 2-[(Diphenylmethyl) thio] acetic acid (5 g) was suspended in purified water (50 ml) at 25 to 3OPreparation of 2-[(Diphenylmethyl)sulfinyl] acetic acid; 2-[(Diphenylmethyl) thio] acetic acid (25 g) was suspended in purified water (100 ml) at 25 to 30Preparation of 2-[(Diphenylmethyl)sulfinyl] acetic acid; Sodium perborate (15.30 g) was suspended in purified water (23 ml) at 25 to 30General procedure: To examine the catalytic activity of the heterogeneous catalyst, 1 mmol of sulde, 1.5 ml of hydrogen peroxide 30 percent as oxidant and 5 percent mol of catalyst weredissolved in 3 ml solvent and reacted at room temperature for different times(Scheme 4; Table 1; Fig. 7). The monitoring of the sulfoxide formation was carried out by TLC (n-hexanes:EtOAc, 1:1 or CHCl3:MeOH, 9:1 as eluent). Aftercompletion of the reaction, the solvent was evaporated and the crude product waspuried by a recrystallization method (using EtOAC/n-hexane) (Table 2). Thecatalyst was recovered and reused for further runs.81.5 g of a 21percent sodium ethoxide solution in ethanol (0.237 mols of sodium ethoxide), kept under inert atmosphere, is added with 28.6 g (0.237 mols) of ethyl mercaptoacetate (14). The stirred mixture is heated to 30-35°C inner temperature and 45 g (0.22 mols) of diphenylchloromethane (13) are added thereto in 15'. After completion of the addition, the mass is kept under stirring at 30-35°C for 4h. After completion of the reaction, 24 ml of a 30percent sodium hydroxide solution (0.239 mols) are added in 15-20', keeping the inner temperature at 30-35°C. After completion of the addition, the mixture is kept under stirring for about 30', then solvents are distilled off until reaching inner temperature of 100°C, gradually adding an equal volume of water to the distillate during the operation. The mass is cooled to 40=45°C inner temperature and 360 ml of a 5percent sodium hypochlorite aqueous solution (0.24 mols) are added, in about 2 hours. 15'After the end of the addition, the mass is cooled to 20 25°C inner temperature, added with 180 ml of toluene and acidified with 88 ml of 50percent sulfuric acid, keeping pH at 2; the precipitated product is filtered, washed with water to neutrality, then squeezed and dried in oven under vacuum at a temperature of 55 60°C, thereby obtaining 44 g (0.16 mols) of 2- [ (diphenylmethyl) sulfinyl] acetic acid (9) (yield: 73percent).Benzhydrylthioacetic acid (19.00 Kg) and glacial acetic acid (57 L) were charged into a reactor and the mass was cooled to about 20+/-3° C. Hydrogen peroxide (50percent; 5.80 L) was slowly added to the mass at about 20+/-3° C. and stirred for about 4 hours. After addition of water (104.50 L) to the mass, it was heated to about 30+/-5° C. and stirred for about 45 minutes. The solid was filtered and washed with water (38 L). The wet cake was dried at about 42.5+/-2.5° C. under reduced pressure for about 6 hours. Ethyl acetate (95 L) was added to the dry solid material and heated at about 67.5+/-2.5° C. for about 45 minutes. The mass was cooled to about 30+/-5° C. and stirred for about 45 minutes. The solid was filtered and washed with ethyl acetate (19 L). The wet cake was dried below 45° C. under reduced pressure for about 7 hours to afford the title compound (yield: 80.23percent).C. Synthesis of 2-(benzhydrylsulfinyl)acetic acid [00104] 10g of thiourea was dissolved in 57 mL of 48percent HBr and 10ml of water. The reaction mixture was heated to 60°C, and 20.2 g of benzhydrol was added. The temperature was increased to 90°C, and the mixture was then cooled to room temperature. The crystals were filtered off and washed with water. To the above crystals were added 35 mL 30percent sodium hydroxide. The mixture was heated to 70°C, and 11.44 g chloroacetic acid in 22 mL of water were added slowly. The mixture was reflux ed for half an hour after the addition. 14.3 mL hydrogen peroxide (30percent) was added to the above solution within 3 hours at room temperature. Water (22 ml) was added to the reaction mixture, which was then filtered. The filtrate was acidified with concentrated HC1 (d=1.18). The resulting solid was filtered and dried to give 2- (benzhydrylsulfinyl)acetic acid (13g, 43percent) as the desired product.

A metabolite of Modafinil, a central nervous system vigilance promoting agent, which possesses neuroprotective properties

Molecular Weight:274.3
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:274.06636548
Monoisotopic Mass:274.06636548
Topological Polar Surface Area:73.6
Heavy Atom Count:19
Complexity:299
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes