2-([(5-CHLORO-1-METHYL-3-PHENYL-1H-PYRAZOL-4-YL)METHYL]SULFANYL)BENZENECARBOXYLIC ACID synthesis

Yield:318234-17-2 99%

Reaction Conditions:

Stage #1: 3-phenyl-5-chloro-4-chloromethyl-1-methyl-1H-pyrazole;Thiosalicylic acidwith potassium carbonate in ethanol;water; for 2 h;Heating / reflux;
Stage #2: with hydrogenchloride in water; pH=2;

Steps:

1.c

To the solution made of 2-mercaptobenzoic acid (1.54 g, 0.01 mol), dry potassium carbonate (1.66 g, 0.012 mol) and water (15 ml), the solution of 3-phenyl-5-chloro- 4-chloromethyl-l-methyl-lH-pyrazole (2.41 g, 0.01 mol) in ethanol (45 ml) is added. The reaction mixture is stirred and heated under reflux conditions for 2 hours and evaporated in vacuum. To the solid white residue water (100 ml) is added and the mixture is acidified to pH = 2 with 10% hydrochloric acid. The white crystalline material is filtered off, washed with water (2 x 25 ml) to obtain 3.56 g (99%) of the title acid, m. p.: 192-193 °C. After recrystallisation from ethanol (130 ml) m. p.: 195- 196 °C. NMR, 8H (400 MHz, DMSO-d6) : 3. 88 (s, 3H, 1-CH3), 4.10 (s, 2H, CH2S), 7.25 (m, 1H), 7. 38 (m, 1H), 7.44 (m, 2H), 7.51 (m, 2H), 7.71 (m, 2H), 7.92 (m, 1H), 11.2 (broad s., 1H, COOH).

References:

WO2005/60959,2005,A1 Location in patent:Page/Page column 16