ChemicalBook CAS DataBase List 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid

5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid synthesis

5synthesis methods

Product Name:5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid
CAS Number:956317-36-5
Molecular formula:C10H9N3O2
Molecular Weight:203.2

52548-14-8

288-36-8

956317-36-5

Step 1) Synthesis of 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid: under nitrogen protection, N,N-dimethylformamide (30 mL), 1,2,3-triazole (3.45 g, 50 mmol), 2-iodo-5-methylbenzoic acid (5.24 g, 20 mmol), caesium carbonate (11.72 g, 36 mmol), trans-N,N'-dimethyl-1,2-cyclohexanediamine (0.51 g, 3.6 mmol) and cuprous iodide (0.38 g, 2 mmol). The reaction mixture was heated to 100 °C for 4 hours. After completion of the reaction, the mixture was cooled to room temperature, diluted with water (60 mL) and extracted with ethyl acetate (200 mL x 2). The aqueous layer was acidified to pH 1 to 2 with concentrated hydrochloric acid and extracted again with ethyl acetate (200 mL x 2). The organic layers were combined, dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum and the residue was purified by silica gel column chromatography (dichloromethane/methanol, v/v=50/1) to give the title compound as a yellow solid (2.76 g, 68%). Mass spectrum (ESI, negative ion) m/z: 202.1 [M-H]-; 1H NMR (CD3OD, 600 MHz) δ (ppm): 7.88 (s, 2H), 7.66 (d, 1H), 7.59 (d, J=8.2 Hz, 1H), 7.50-7.48 (dd, J=8.1 Hz, 1.1 Hz, 1H), 2.45 ( s, 3H); 13C NMR (CD3OD, 151MHz) δ (ppm): 169.8, 140.7, 137.5, 136.7, 133.5, 131.5, 129.3, 126.0, 21.0.

288-36-8 Synthesis

288-36-8
469 suppliers
$6.00/1g

52548-14-8 Synthesis

52548-14-8
223 suppliers
$9.00/1g

956317-36-5
245 suppliers
$7.00/250mg

Yield:956317-36-5 93%

Reaction Conditions:

Stage #1:2-iodoyl-5-methylbenzoic acid with potassium carbonate in acetone at 55 - 60; for 0.5 h;Large scale;
Stage #2:1,2,3-triazole with copper(l) iodide in acetone at 55 - 60; for 8 h;Large scale;Temperature;

Steps:

1; 2; 3; 4; 5 Example 2
Add 1.1 kg of acetone to the 5L reaction flask.131g 2-iodo-5-methylbenzoic acid,Stir and dissolve,Add 350g of anhydrous potassium carbonate,After heating to reflux (55-60 ° C) for half an hour, add 114g 1,2,3-triazole,2.4 g of cuprous iodide.The reaction was kept under reflux (55-60 ° C) for 8 hours, sampled, and sampled once every 1 h. After the reaction was completed, it was cooled to room temperature for filtration, and the filter cake was washed twice with 120 g of acetone to obtain a white solid at room temperature (20-30 ° C). The white solid was dissolved in 1.3 kg of purified water and stirred.After 30 min, hydrochloric acid was added dropwise at room temperature to adjust the pH of the system to 1.5-2.0 to obtain a large amount of white solid. It was stirred for 1-2 hours, filtered, and the filter cake was washed twice with purified water. The resulting solid was dried to dryness at 50 ± 5 ° C to give a crude compound.Add 1 compound of crude product, 0.2 kg of absolute ethanol and 0 kg of purified water to a 1 L reaction flask, and warm to 75-80 ° C.Clear, heat for half an hour, cool to 0-5 ° C, filter, filter cake with a cold ethanol solution rinse, to obtain a white solid compound 1 boutique.The compound 1 was placed in a blast drying oven at a temperature of 55 ° C ± 5 ° C and dried for 5 h. Sampling, sampling every 2h 1Time, until the test (rapid moisture analyzer: 105 ° C, 10 min) loss on drying ≤ 0.5%, get Suwoleisheng intermediate products -Compound 1 was fine white crystalline solid 86 g, yield: 93%. Purity: 99.91%, Cu < 5 ppm.

References:

Yangzijiang Pharmaceutical Group Co., Ltd.;Zou Yiquan;Xu Jingren;Cai Wei;Xuan Jingan;Chen Lingwu;Ji Ye;Zhu Yunlong;Liu Jinfeng;Hu Tao CN109810067, 2019, A Location in patent:Paragraph 0027-0041

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288-36-8 Synthesis

288-36-8
469 suppliers
$6.00/1g

52548-14-8 Synthesis

52548-14-8
223 suppliers
$9.00/1g

956317-36-5
245 suppliers
$7.00/250mg