Preparation of 2-([1,2,3]triazol-2-yl)-benzoic acid derivatives
A technology for benzoic acid and derivatives, which is applied in the field of preparation of 2-([1,2,3]triazol-2-yl)-benzoic acid derivatives, can solve problems such as not being significantly upgraded, and achieves easy access to , the effect of low cost
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Embodiment 11
[0238] Example 1.1: Crystalline 5-methoxy-2-(2H-1,2,3-triazol-2-yl)benzoic acid potassium salt (5-methoxy-2-(2H-1,2,3 -triazol-2-yl)potassium benzoate)
[0239] 2-Bromo-5-methoxybenzoic acid (21.5g, 0.093mol, 1eq.), copper (I) iodide (0.886g, 0.05eq.) and K 2 CO 3 The powder (32.2 g, 2.5 eq.) was suspended in dioxane (600 mL) and water (8.4 mL). Add 1H-1,2,3-triazole (10.8mL, 2eq.) and trans-N,N-dimethylcyclohexane-1,2-diamine (1.32g, 0.1eq.) to the mixture . The mixture was heated at reflux for 3.5 h. IPC shows full conversion. The ratio of desired N(2) to regioisomeric N(1) isomer was 84:16. The mixture was cooled to 40°C and filtered. The filter cake was washed with dioxane (100 mL). The solid was dried to obtain 50.6 g of a blue solid. The ratio of N(2) to N(1) isomers was 98.6:1.4.
[0240] Table 1: Characterization data for 5-methoxy-2-(2H-1,2,3-triazol-2-yl)benzoic acid potassium salt in crystalline form 1
[0241] technology Data overview annot...
Embodiment 12
[0242]Example 1.2: Crystalline 5-methoxy-2-(2H-1,2,3-triazol-2-yl)benzoic acid
[0243] The solid from Example 1.1 was dissolved in water (300 mL). TBME (200 mL) and 32% aqueous HCl (35 mL) were added. Separate the aquifer and discard it. The organic layer was washed with a mixture of 2N aqueous HCl (100 mL) and 32% aqueous HCl (20 mL). The organic layer was washed with 1N aqueous HCl (50 mL). The organic layer was extracted with 1N aqueous NaOH (200 mL). The aqueous layer was heated to 45 °C and traces of TBME were removed under reduced pressure. To the aqueous layer was added 32% aqueous HCl (20 mL) at 45 °C. At pH 6, seed crystals are optionally added. At 40°C, the resulting suspension was filtered. The filter cake was washed with water (30 mL). The product was dried at 60°C and 5 mbar. Yield: 12.4 g, 61%. Purity: 100% a / a,t R 0.63min. Seed crystals were obtained by careful crystallization according to the above procedure.
[0244] MP: 80°C (DSC).
[0245] 1...
Embodiment 13
[0248] Example 1.3: Crystalline 5-methoxy-2-(2H-1,2,3-triazol-2-yl)benzoic acid potassium salt
[0249] For example, 5-methoxy-2-(2H-1,2,3-triazol-2-yl)benzoic acid (5g, 0.0228mol) obtained according to the steps of Reference Example 1 and KHCO 3 (1.61g, 0.7eq) was suspended in dioxane (100mL) and water (1mL). The mixture was heated at reflux for 40 min. The mixture was cooled to 20°C and filtered. Yield: 2.56 g, 44%. 1 H NMR (400MHz, D2O) δ: 3.80 (s, 3H), 7.04 (m, 2H), 7.46 (d, J = 8.7Hz, 1H), 7.82 (s, 2H). MP: 279.5°C (DSC additionally exhibited a broad endotherm at about 153°C to 203°C attributable to endothermic desolvation; melting was followed by exothermic decay).
[0250] Table 3: Characterization data for 5-methoxy-2-(2H-1,2,3-triazol-2-yl)benzoic acid potassium salt in crystalline form 2
[0251] technology Data overview annotation XRPD crystallization see image 3
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