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Preparation method and application of 1-aryl-2-(1,2,4-triazole-1-group) ethanol
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A technology of reaction and dichlorophenyl, which is applied in the field of preparation of 1-aryl-2-ethanol, can solve the problems of high isomer content and low content of crude propiconazole, and achieves high product purity and novel preparation process , improve the effect of selectivity
Inactive Publication Date: 2013-01-23
HUNAN UNIV
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[0014] Therefore, the content of the crude product of propiconazole obtained by the existing production technology process is not high (80%~82%), mainly because the content of isomers is high (10%~15%)
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Embodiment 1
[0055] Preparation of 2-(2,4-dichlorophenyl)oxirane
[0056]
Embodiment 2
[0059] Preparation of 1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethanol
[0060]
[0061] 0.12mol 2-(2,4-dichlorophenyl)oxirane, 0.03mol potassiumhydroxide and 0.5gDBU, 0.12mol1,2,4-triazole, 50mL N-methylpyrrolidone, stirred at reflux for 6h, reacted After completion, neutralize with hydrochloric acid, separate phases, cool the organic phase, crystallize, filter, and dry to obtain white solid 1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl) Ethanol, yield 72.5%, m.p.74~78℃; 1 H NMR (400MHz, CDCl 3 +D 2 O)δ: 4.20 (dd, J=14.0, 8.0Hz, 1H, OCH), 4.55 (dd, J=14.0, 2.0Hz, 1H, NCH 2 ), 5.42 (dd, J = 8.0, 2.0Hz, 1H, NCH 2 ), 7.29 (dd, J=8.4, 2.0Hz, 1H, C 6 h 3 5-H), 7.40(d, J=2.0Hz, 1H, C 6 h 3 3-H), 7.51(d, J=8.4Hz, 1H, C 6 h 3 6-H), 7.92(s, 1H, C 2 h 2 N 3 ), 8.09(s, 1H, C 2 h 2 N 3 ).
Embodiment 3
[0063] Preparation of 1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethanone
[0064]
[0065] Dissolve 0.1mol l-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethanol in 300ml acetone, cool to 0°C, add 0.11mol Jones reagent dropwise, The reaction solution was stirred at 0 °C for 0.5 h. Diluted with 150ml of water, extracted with 250ml of ethyl acetate, and distilled under reduced pressure to obtain 1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethanone with a yield of 72.7 %, mp.100~103℃; 1 H NMR (400MHz, CDCl 3 )δ: 5.65(s, 2H, CH 2 ), 7.40 (dd, J=8.4, 2.0Hz, 1H, C 6 h 3 5-H), 7.52(d, J=2.0Hz, 1H, C 6 h 3 3-H), 7.67(d, J=8.4Hz, 1H, C 6 h 3 6-H), 8.01(s, 1H, triazole C 2 h 2 N 3 5-H), 8.30(s, 1H, triazole C 2 h 2 N 3 3-H).
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Abstract
The invention discloses a preparation method of 1-aryl-2-(1,2,4-triazole-1-group) ethanol shown as a formula I. X1 and X2 are selected from H, CH3, CH3CH2, F3C, CH3O, CH3CH2O, NO2, CN, C1, Br or F. The preparation method comprises the following processes of: performing epoxidation reaction on sulfurylide [(CH3)3S+CH3SO4<->] and arylformaldehyde to prepare 2-arylethyleneoxide; and reacting the2-aryl ethyleneoxide and 1,2,4-triazole in a solvent under the action of a catalyst and alkali (OH-) to generate the 1-aryl-2-(1,2,4-triazole-1-group) ethanol (I). The 1-aryl-2-(1,2,4-triazole-1-group) ethanol is applied in preparation of a compound (such as pentyl cyclozole, methyl cyclozole, ethyl cyclozole or propyl cyclozole) shown as a formula II, wherein R is selected from H, CH3, CH2CH3 or CH2CH2CH3.
Description
technical field [0001] The invention relates to a preparation method and application of a key intermediate, in particular to a preparation method and application of 1-aryl-2-(1,2,4-triazol-1-yl)ethanol. Background technique [0002] The compound shown in the chemical structural formula II is a class of efficient broad-spectrum fungicides: [0003] [0004] Among them, penconazole (IIa): X 1 =X 2 =Cl, R=H; Metroconazole (IIb): X 1 =X 2 = Cl, R = CH 3 ; Ethiconazole (IIc): X 1 =X 2 = Cl, R = CH 2 CH 3 ; propiconazole (IId): X 1 =X 2 = Cl, R = CH 2 CH 2 CH 3 ; [0005] Chinese patent [CN101323612] and literature [Fine Chemical Intermediates, 2007, 36 (1): 25; Shandong Chemical Industry, 2007, 36 (9): 17] describe that propiconazole is mainly 2,4-dichlorophenethyl Ketones are raw materials and are produced through the following two process routes: [0006] 1) The process route of first cyclization and then condensation after bromination: [0007] [0008] ...
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