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Method for preparing Tebucomazole in high purity

A technology of pure tebuconazole and tebuconazole, applied in the field of synthesis of pesticide tebuconazole-1--3-pentanol), can solve the problems of yield lower than 76%, difficult separation, no bactericidal activity and the like, Achieving the effect of high purity, convenient operation and high yield

Inactive Publication Date: 2007-09-12
HUNAN CHEM RES INST +1
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0004] The main impurity in the synthesized tebuconazole is the isomer by-product generated in the ring-opening reaction—4,4-dimethyl-3-(4H-1,2,4-triazol-4-ylmethyl) -1-(4-chlorophenyl)-3-pentanol (2), because 2 is similar to 1 in nature, it is not easy to separate, resulting in a product purity of only 95%, and the yield is lower than 76% (with 1-(4-chloro Phenylethyl)-1-tert-butyl-1,2-oxirane, 3 counts)
Because in 1,2,4-triazole compounds, the 1-substituent derivatives have bactericidal activity, and the 4-substituent derivatives have no bactericidal activity

Method used

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  • Method for preparing Tebucomazole in high purity
  • Method for preparing Tebucomazole in high purity
  • Method for preparing Tebucomazole in high purity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 120g (0.40mol)3, 3g (0.05mol) of potassium hydroxide, 40g (0.55mol) of 1,2,4-triazole, 1g of N,N-dimethyl-4-aminopyridine, and 100mL of n-butanol A 500mL three-necked flask with a stirring and reflux tube was stirred for 6 hours at a reflux temperature of 120°C. After the reaction was complete, hydrochloric acid was added for neutralization and phase separation. The organic phase was cooled and crystallized, filtered and dried to obtain 102g of a white solid, w(1)≥98.0% (liquid Phase chromatography, external standard), yield ≥ 81.4% (based on 3). Melting point 102-104°C (literature value: melting point 102-104°C).

[0027] The spectrogram data of tebuconazole 1 is as follows ESI-MS (m / z); 308 (M + ). 1 H NMR (400MHz, CDCl 3 ), δ: 1.03(s, 9H, C(CH 3 ) 3 ), 1.67 (tt, J = 14.0Hz, 4.0Hz, 1H, CH 2 ), 1.82 (m, 2H, CH 2 CH 2 ), 2.44(tt, J=14.0Hz, 4.0Hz, 1H, CH 2 ), 3.01(s, 1H, OH), 4.33(d, J=14.4Hz, 1H, CH 2 ), 4.38 (d, J=14.4Hz, 1H, CH 2 ), 6.95 (d, J=8.4Hz, 2H...

Embodiment 2

[0029] Add 120g (0.40mol)3, 6g (0.10mol) of potassium hydroxide, 40g (0.55mol) of 1,2,4-triazole, 1g of N,N-dimethylaniline, and 100mL of dimethylformamide with stirring and a 500mL three-neck flask with a reflux tube, stirred at 130°C for 4h, after the reaction was complete, added hydrochloric acid to neutralize, and the solvent was recovered by distillation under sub-pressure, the organic phase was cooled and crystallized, washed with water, filtered and dried to obtain 106g of a white solid, w(1)≥98.6% (liquid Phase chromatography, external standard), the yield ≥ 85.0% (calculated as 3).

Embodiment 3

[0031] 120g (0.40mol)3, 7g (0.10mol) of sodium ethoxide, 40g (0.55mol) of 1,2,4-triazole, 0.5g of N,N-dimethyl-4-aminopyridine, and 100mL of n-butanol were added to the A 500mL three-neck flask with a stirring and reflux tube was stirred at 120°C for 6h. After the reaction was completed, hydrochloric acid was added to neutralize, and the solvent was recovered by distillation under secondary pressure. The organic phase was cooled and crystallized, filtered and dried to obtain 101g of a white solid, w (1) ≥ 98.3% ( liquid chromatography, external standard), the yield ≥ 80.7% (calculated as 3).

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Abstract

A process for preparing high-purity pentazolol features the reaction between 1-(4-chlorphenylethyl)-1-tert-butyl-1, 2-epoxy ethane and 1,2,4-triazole in organic polar solvent under existence of alkali while adding catalyst chosen from N,N-dimethyl-4-aminopyridine, N,N-dimethylphenylamine, methylphrrolidone, dimethyl formamide, methanol sodium, ethanol sodium, potassium hydroxide and sodium hydroxide. Its advantages are high output rate and high purity.

Description

technical field [0001] The invention relates to a pesticide tebuconazole (4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)-1-(4-chlorophenyl)-3 -amyl alcohol) synthetic method. Background technique [0002] Tebuconazole (4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)-1-(4-chlorophenyl)-3-pentanol, 1) , is a low-toxic and high-efficiency triazole fungicide developed by Bayer Company of Germany, and a sterol demethylation inhibitor, which is used for seed treatment or foliar spraying of important economic crops. Its structural formula is: [0003] [0004] The main impurity in the synthesized tebuconazole is the isomer by-product generated in the ring-opening reaction—4,4-dimethyl-3-(4H-1,2,4-triazol-4-ylmethyl) -1-(4-chlorophenyl)-3-pentanol (2), because 2 is similar to 1 in nature, it is not easy to separate, resulting in a product purity of only 95%, and the yield is lower than 76% (with 1-(4-chloro phenethyl)-1-tert-butyl-1,2-oxirane, 3 g). Because in 1,2,4-triazole comp...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/08
Inventor 胡艾希王宇张建宇
Owner HUNAN CHEM RES INST
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