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Synthetic method of 2-hydroxy propanedinitrile

A technology of hydroxypropanedicyanide and a synthesis method, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of short reaction time, low cost, harsh reaction conditions, etc., and achieves short reaction time and cost. Low, simple post-processing effects

Inactive Publication Date: 2013-02-20
SHANGHAI STA PHARMA R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of this invention is to provide a kind of reaction time is short, and cost is low, is suitable for the chemical synthesis method of the 2-hydroxy propanedicyanide of large-scale industrial production, mainly solves the concrete operation that existing synthetic method exists, and reaction condition is harsh, and reaction time Long, low implementability, impractical for industrial production

Method used

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  • Synthetic method of 2-hydroxy propanedinitrile
  • Synthetic method of 2-hydroxy propanedinitrile
  • Synthetic method of 2-hydroxy propanedinitrile

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Effect test

Embodiment 1

[0015]

[0016] Trifluoroacetic anhydride (14mL, 0.1mol) was added dropwise to urea hydrogen peroxide (9.4g, 0.1mol) and dichloromethane (100 mL) at 0°C, and then stirred at room temperature for 3 hours to obtain trifluoroperoxy acetic acid. Dissolve 2-(1-hydroxyacetal) propanedicyanide sodium salt (13g, 0.1mol) in 150 mL water, add trifluoroacetic acid (7.79 mL, 0.2mol) at 0°C, and then add the peroxy Trifluoroacetic acid was added dropwise, stirred at 35°C for 2 hours, and the reaction was completed by TLC analysis. The reaction solution was quenched with a 2 mol / liter sodium sulfite aqueous solution, the reaction solution was extracted with ethyl acetate, separated, dried over anhydrous sodium sulfate, filtered and concentrated in vacuum at low temperature to obtain an oily liquid product 2-hydroxypropanedicyanide (6.6g, 80 %). 1 HNMR (400 MHz, CD 3 OD): d 5.74 (s, 1H).

Embodiment 2

[0018]

[0019] Acetic anhydride (9 mL, 0.1 mol) was added dropwise to urea hydrogen peroxide (9.4 g, 0.1 mol) and dichloromethane (100 mL) at 0°C, and then stirred at room temperature for 1 hour to obtain peracetic acid. Dissolve 2-(1-hydroxyacetal)propanedicyanide sodium salt (13g, 0.1mol) in 150 mL water, add acetic acid (28.8 mL, 0.5mol) at 0°C, and then drop the previously prepared peracetic acid Add it in, stir at 25°C for 4 hours, and the reaction is complete as detected by thin-layer analysis. The reaction solution was quenched with 2 mol / L sodium sulfite aqueous solution, the reaction solution was extracted with ethyl acetate, separated, dried over anhydrous sodium sulfate, filtered and concentrated in vacuum at low temperature to obtain the oily liquid product 2-hydroxypropanedicyanide (6.1 g, 74 %). 1 HNMR (400 MHz, CD 3 OD): d 5.74 (s, 1H).

Embodiment 3

[0021]

[0022] Trifluoroacetic anhydride (14mL, 0.1mol) was added dropwise to urea hydrogen peroxide (9.4g, 0.1mol) and dichloromethane (100mL) at 0°C, then stirred at room temperature for 2 hours to obtain trifluoroperoxy acetic acid. Dissolve 2-(1-hydroxyacetal) propanedicyanide (10.8g, 0.1mol) in 150 mL of water, add acetic acid (11.52 mL, 0.2mol) at 0°C, and then add peroxytrifluoroacetic acid prepared above Add it dropwise, and stir at 25°C for 6 hours. TLC analysis detects that the reaction is complete. The reaction solution was quenched with 2 moles / liter of sodium sulfite aqueous solution, the reaction solution was extracted with ethyl acetate, separated, dried over anhydrous sodium sulfate, filtered and concentrated in vacuum at low temperature to obtain the oily liquid product 2-hydroxypropanedicyanide (7g, 85% ). 1 HNMR (400 MHz, CD 3 OD): d 5.74 (s, 1H).

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Abstract

The invention relates to a practical synthetic method of 2-hydroxy propanedinitrile based on a chemical synthesis method, mainly solving the problems of conventional synthetic method that the specific operation is complex, the reaction condition is severe, the reaction time is long, the performability is low, and the industrial production cannot be carried out. According to the synthetic method, the conventional 2-(1-hydroxy acetal) propanedinitrile which is easy to obtain is adopted and reacts with peroxy acid to generate the 2-hydroxy propanedinitrile, wherein the peroxy acid is prepared by acetic anhydride or trifluoroacetic anhydride and urea hydrogen peroxide. The chemical synthetic method of 2-hydroxy propanedinitrile provided by the invention is brand new, short in reaction time, low in cost, and suitable for industrial scale production.

Description

technical field [0001] The present invention relates to a kind of synthetic method of 2-hydroxy propanedicyanide. Background technique [0002] 2-Hydroxymalonocyanide is an important intermediate in the synthesis of dimethyl-tert-butylsilyl-protected 2-hydroxymalonylcyanide or acetyl-protected 2-hydroxymalonylcyanide. The 2-hydroxyl propanedicyanide protected by dimethyl tert-butyl silicon or the 2-hydroxyl propanedicyanide protected by acetyl group is a new type of reagent, which can quickly and efficiently synthesize the alpha hydroxy ester or a Hydroxyamide. As a novel and efficient reaction reagent, there is no report on the synthesis method suitable for the industrial production of 2-hydroxymalonocyanide. As reported in Journal of Physical Chemistry A (2001), 105(26), 6543-6551): [0003] [0004] The existing literature reports that the raw materials are not easy to obtain, the reaction conditions are harsh, the reaction time is long, the yield is low, the feasib...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/16C07C253/30
Inventor 张治柳林小娟于海宇吴成德马汝建陈曙辉
Owner SHANGHAI STA PHARMA R&D CO LTD
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