Preparation method of chiral optical pure p-toluene sulfamide

A technology of toluene sulfinamide and sodium toluene sulfinamide is applied in the field of preparation of chiral optically pure p-toluene sulfinamide, which can solve the problems of unfavorable large-scale production, large solvent ratio and high price of LiHMDS, and achieves atomic utilization rate High, improve alkalinity, cost saving effect

Active Publication Date: 2018-09-21
SHANGHAI TIANYE CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] In the above method, the price of LiHMDS used is higher, and the proportion of solvent used is relatively large, and it is only effective for (S)-p-toluene sulfinamide, which is not conducive to large-scale production

Method used

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  • Preparation method of chiral optical pure p-toluene sulfamide
  • Preparation method of chiral optical pure p-toluene sulfamide
  • Preparation method of chiral optical pure p-toluene sulfamide

Examples

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Embodiment 1

[0041] The first step: the synthesis of p-toluenesulfinyl chloride.

[0042] (1) Put 267g of toluene, 53.4g of sodium p-toluene sulfinate and 0.1g of N,N-dimethylformamide into a dry and clean 500mL four-necked bottle with an addition funnel, add 57.5g of thionyl chloride dropwise at room temperature, React at 55-65°C for 4 hours, take samples for GC or HPLC detection after derivatization, the raw material is less than 0.3%, concentrate under reduced pressure, replace once with 150g of toluene, then add 50g of toluene to dilute for later use. The external standard yield is 94%.

[0043] (2) Put 267g of benzene, 53.4g of sodium p-toluenesulfinate and 0.1g of N,N-dimethylformamide into a dry and clean 500mL four-necked bottle with an addition funnel, add 57.5g of thionyl chloride dropwise at room temperature, and Reaction at 55-65°C for 4 hours, sampled by GC or HPLC after derivatization, the raw material is less than 0.3%, concentrated under reduced pressure, replaced once wit...

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Abstract

The invention discloses a preparation method of chiral optical pure p-toluene sulfamide. The preparation method comprises the following steps: performing acylating chlorination by using sodium p-tolylsulfinate and an acylating chlorination reagent to obtain p-toluene sulfonyl chloride, then mixing the p-toluene sulfonyl chloride with hydrazine hydrate to obtain p-toluene sulfonyl hydrazine, performing separation and dissociation with a tartaric acid resolving agent, and performing splitting decomposition with zinc acetate to obtain the pure p-toluene sulfamide. The process disclosed by the invention is easy and convenient to operate, stable, high in yield and environmentally friendly. Compared with the conventional process, the preparation method has the advantages that the raw materials are easy to obtain, the production cost of the existing chiral optical pure p-toluene sulfamide is substantially reduced, and the industrial large-scale production is facilitated.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a preparation method of chiral optically pure p-toluene sulfinamide. Background technique [0002] p-toluenesulfinamide, English name p-toluenesulfinamide molecular formula: C7H9NOS. Including R-type and S-type configurations, the English names correspond to (R)-p-toluenesulfinamide and (S)-p-toluenesulfinamide respectively. Since it was first synthesized in the middle of last century, it has been used as one of the key chiral sources of chiral amine drugs and their intermediates. Especially widely in academics, it is an important chemical as a chiral prosthetic group, which is of great significance in chiral synthesis and chiral drug synthesis. Nowadays, most of the drugs or drug intermediates have amine groups, and in many reports, chirally optically pure p-toluenesulfinamides are a flexible source of diastereomers in asymmetric synthesis. [0003] Bot...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C313/02C07C313/04C07C313/06C07C51/41C07C59/255
CPCC07B2200/07C07C51/412C07C313/02C07C313/04C07C313/06C07C59/255
Inventor 高峰曾赛兰
Owner SHANGHAI TIANYE CHEM
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