Method for preparing (1-methyl-1H-[1,2,4] triazole-3-yl)-methyl alcohol

A technology of trityloxyacetamide and methyl, applied in the field of preparation of -methanol, can solve the problems of difficulty in obtaining, cumbersome steps and high price, and achieves the effects of low price, high operational safety and less waste water

Active Publication Date: 2018-04-06
SHANGHAI TBBMED CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are relatively few reports about the synthetic method of this compound at present, and the method reported in Chem.Pharm.Bul.42 (1) 85-94,1994 is to be raw material with 1H-[1,2,4]triazole-3-carbinol, After protecting the hydroxyl group with tert-butyldimethylchlorosilane, react with methyl iodide under the action of sodium hydride, and then remove the protecting group in methanol solution of sodium hydroxide to obtain the target product (1-methyl-1H-[1 ,2,4]triazole-3-yl)-methanol, the method steps are loaded down with trivial details, and the raw material 1H-[1,2,4]triazole-3-methanol price used is high, and is difficult for obtaining, has limited (1-methanol Industrial production of 1H-[1,2,4]triazol-3-yl)-methanol

Method used

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  • Method for preparing (1-methyl-1H-[1,2,4] triazole-3-yl)-methyl alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] In the first step, add 50g (0.666mol, 1.0eq) of 2-hydroxyacetamide and 500mL of dichloromethane into a 1L three-necked flask with a mechanical stirrer and a thermometer, start stirring, and then add 204.1g (0.732mol, 1.1 eq) triphenylchloromethane and 87.6g (0.866mol, 1.3eq) triethylamine, slowly warm up to reflux, keep warm for 2h, the raw materials controlled in GC react completely, cool down, add 100mL water, stir for 30min, let stand and separate, Separate the lower organic phase, then extract the aqueous phase with 100 mL of dichloromethane, combine the organic phases, and concentrate the organic phase under reduced pressure to obtain a crude product, which is slurried with ethyl acetate / n-heptane (1:4), suction filtered, and dried to obtain White solid 2-trityloxyacetamide 192.3g, yield 91%, purity 98.2% (HPLC), mp 175-177°C, MS (m / z) 317.1 (M+H) + .

[0020] In the second step, add 192.3g (0.606mol, 1.0eq) 2-trityloxyacetamide and 1L ethyl formate in a 2L three-...

Embodiment 2

[0023] In the first step, add 50g (0.666mol, 1.0eq) 2-hydroxyacetamide and 500mL tetrahydrofuran into a 1L three-necked flask with a mechanical stirrer and a thermometer, start stirring, and then add 222.8g (0.799mol, 1.2eq) Triphenylchloromethane and 79.0g (0.999mol, 1.5eq) pyridine, slowly raise the temperature to reflux, keep warm for 2h, the reaction of the raw material controlled in GC is complete, cool down, add 100mL of water, stir for 30min, let stand for stratification, and separate the lower organic phase, then extract the aqueous phase with 100mL dichloromethane, combine the organic phases, and concentrate the organic phase under reduced pressure to obtain a crude product. The crude product is slurried with ethyl acetate / n-heptane (1:4), filtered by suction, and dried to obtain a white solid 2- Trityloxyacetamide 194.4g, yield 92%, purity 98.3% (HPLC), mp 175-177°C.

[0024] In the second step, add 194.4g (0.613mol, 1.0eq) 2-trityloxyacetamide and 1L ethyl formate i...

Embodiment 3

[0027] In the first step, add 50g (0.666mol, 1.0eq) 2-hydroxyacetamide and 500mL methyl tert-butyl ether into a 1L three-necked flask with a mechanical stirrer and a thermometer, start stirring, and then add 185.7g (0.666 mol, 1.0eq) of triphenylchloromethane and 103.3g (0.799mol, 1.2eq) of diisopropylethylamine, slowly warming up to reflux, keeping warm for 2h, the reaction of the raw materials controlled in GC is complete, cooling down, adding 100mL of water, stirring for 30min, Stand to separate the layers, separate the lower organic phase, then extract the aqueous phase with 100mL methyl tert-butyl ether, combine the organic phases, and concentrate the organic phase under reduced pressure to obtain the crude product. The crude product was washed with ethyl acetate / n-heptane (1:4 ) beating, suction filtration, and drying to obtain 190.2 g of white solid 2-trityloxyacetamide, yield 90%, purity 98.1% (HPLC), mp 175-177°C.

[0028] In the second step, add 190.2g (0.599mol, 1.0...

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Abstract

The invention discloses a method for preparing (1-methyl-1H-[1,2,4] triazole-3-yl)-methyl alcohol, belonging to the technical field of organic chemistry. The method comprises the following steps: by taking 2-glycolamide as a raw material, protecting hydroxy by adopting triphenylmethyl; carrying out formylation reaction on 2-glycolamide and ethyl formate, and performing condensation ringclosure deprotection with methylhydrazine to obtain (1-methyl-1H-[1,2,4] triazole-3-yl)-methyl alcohol. According to the preparation method, the yield is high, the cost is low, operation condition can be easilycontrolled, and the preparation method is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of (1-methyl-1H-[1,2,4]triazol-3-yl)-methanol, belonging to the technical field of organic synthesis. Background technique [0002] (1-Methyl-1H-[1,2,4]triazol-3-yl)-methanol, English name: (1-Methyl-1H-[1,2,4]triazol-3-yl)-methanol (CAS 135242-93-2), a colorless needle crystal, is a key intermediate in the synthesis of compounds with antifungal activity. There are relatively few reports about the synthetic method of this compound at present, and the method reported in Chem.Pharm.Bul.42 (1) 85-94,1994 is to be raw material with 1H-[1,2,4]triazole-3-carbinol, After protecting the hydroxyl group with tert-butyldimethylchlorosilane, react with methyl iodide under the action of sodium hydride, and then remove the protecting group in methanol solution of sodium hydroxide to obtain the target product (1-methyl-1H-[1 ,2,4]triazole-3-yl)-methanol, the method steps are loaded down with trivial details, and the raw...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08
CPCC07B2200/13C07D249/08
Inventor 高峰曾赛兰蒋军强张行行
Owner SHANGHAI TBBMED CO LTD
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