3-(Methylthio)benzoic acid synthesis
- Product Name:3-(Methylthio)benzoic acid
- CAS Number:825-99-0
- Molecular formula:C8H8O2S
- Molecular Weight:168.21
90721-40-7
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Yield:825-99-0 97%
Reaction Conditions:
Stage #1:3-methanesulfanyl benzoic acid methyl ester with sodium hydroxide;water in tetrahydrofuran;methanol at 70; for 1 h;
Stage #2: with hydrogenchloride in water; pH=2
Steps:
102 Example 102; 3-METHYLSULFANYL-BENZOIC acid
Methyl iodide (0.972 mL) was added to a mixture of 3-mercapto-benzoic acid (601 mg, 3.9 mmol) and potassium carbonate (2.7 g, 19.5 mmol) in DMF (8 mL) in an ice-bath. After the reaction was warmed to room temperature and stirred for 1 hour, the reaction mixture was diluted with ethyl acetate, washed with water (3X), dried over anhydrous sodium sulfate, filtered, and concentrated to afford 3-methylsulfanyl-benzoic acid methyl ester (684 mg, 96%, yellow [OIL). 1H] NMR [(CDC13),] [S] (ppm): 7.90 (s, 1H), 7.80 (d, [1H),] 7.44 (d, 1H), 7.35 (t, 1H), 3.92 (s, 3H), 2.53 (s, 3H). 3-Methylsulfanyl-benzoic acid methyl ester (684mg, 3.8 mmol) and 1N [NAOH] (5.6 mL, 5.6 mmol) in methanol (8 [ML)] and THF (8 mL) were heated at [70°C] for 1 hour. The reaction mixture was concentrated and then the residue was diluted with water. After acidification with 1N [HC1] to [PH-2,] the aqueous layer was extracted with ethyl acetate and then washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 3-methylsulfanyl-benzoic acid (616 mg, 97%, white [SOLID). 1H] NMR (DMSO), [8] (ppm): 13.1 (bs, [1H),] 7.76 (s, 1H), 7.70 (d, 1H), 7.51 (d, 1H), 7.44 (t, 1H), 2.52 (s, 3H).
References:
ASTRA ZENECA AB;NPS PHARMACEUTICALS, INC. WO2004/14881, 2004, A2 Location in patent:Page 136
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825-99-0
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