Process method for synthetizing tert-butyl sulfinamide

A technology of tert-butylsulfinamide and process method, which is applied in the field of synthesis of organic compounds, and achieves the effects of good process stability, reduced production cost, and easy procurement

Active Publication Date: 2013-08-28
DALIAN NETCHEM CHIRAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These unfavorable reaction characteristics limit the large-scale industrial synthesis of (S or R)-tert-butylsulfinamide, so looking for a synthetic process that can avoid cryogenic ultra-low temperature, reduce the amount of ammonia gas, remove foul smell, and be suitable for industrial production is very necessary

Method used

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  • Process method for synthetizing tert-butyl sulfinamide

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Comparison scheme
Effect test

Embodiment 1

[0028] A kind of technical method of synthesizing tert-butyl sulfinamide, synthetic route is as follows:

[0029] The specific steps are:

[0030] Example 1

[0031] a) Synthesis of N-methyltriphenylamine: under argon protection, add triphenylchloromethane (0.1076 mol) to a 1-liter reaction flask equipped with mechanical stirring and cooling bath, and maintain the temperature at -50 Between -60°C, slowly feed 600mL of liquid ammonia, add toluene with 1% triphenylchloromethane mass as internal standard analysis, triphenylchloromethane internal standard analysis is less than 1%, and the reaction stops after 4-6 hours. The reaction solution was raised to room temperature, and the ammonia gas was volatilized. Add 500mL methyl tert-butyl ether (MTBE), wash the organic layer with 70g mass concentration of 10% sodium carbonate, wash the organic layer with 75g*2 water, dry and concentrate to obtain N-methyl Triphenylamine crude product 24g. 1.5*24g diethyl ether beating, filter a...

Embodiment 2

[0036] A kind of processing method of synthesizing tert-butylsulfinamide, reaction formula is as embodiment 1, and concrete steps are:

[0037] a) Synthesis of N-methyltriphenylamine: under the protection of argon, add triphenylchloromethane (0.1076 mol) to a 1-liter reaction flask equipped with mechanical stirring and cold bath, and maintain the temperature at -60 Between ~-70°C, slowly inject 600mL of liquid ammonia, add toluene with 1% mass of triphenylchloromethane as the internal standard analysis, the internal standard analysis of triphenylchloromethane is less than 1%, and the reaction stops after 4-6 hours. The reaction solution was raised to room temperature, and the ammonia gas was volatilized. Add 500mL ethyl acetate, wash the organic layer with 70g mass concentration of 10% sodium carbonate, wash the organic layer with 75g*2 water, dry and concentrate to obtain the crude product of N-methyltriphenylammonia 25.5 g. 1.5*25.5g n-hexane beating, filter after 1.5h, and...

Embodiment 3

[0042] A kind of processing method of synthesizing tert-butylsulfinamide, reaction formula is as embodiment 1, and concrete steps are:

[0043] a) Synthesis of N-methyltriphenylammonia: under the protection of argon, add triphenylbromethane (0.1076 mol) to a 1-liter reaction flask equipped with mechanical stirring and cold bath, and maintain the temperature at -60~ Between -70°C, slowly feed 600mL of liquid ammonia, add toluene with 1% mass of triphenylbromomethane as internal standard analysis, triphenylbromomethane internal standard analysis is less than 1%, and the reaction stops after 4-6 hours. The reaction solution was raised to room temperature, and the ammonia gas was evaporated. Add 500mL MTBE, wash the organic layer with 70g mass concentration of 10% sodium carbonate, wash the organic layer with 75g*2 water, dry and concentrate to obtain 26g of crude N-methyltriphenylamine. 1.5*26g of diethyl ether was beaten, filtered after 1.5h, and the dried product was 0.0930mol....

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Abstract

The invention relates to a method for synthetizing an organic compound. A process method for synthetizing tert-butyl sulfinamide comprises the following steps: (a) under the temperature of between 50 DEG C below zero to 70 DEG C below zero, adding triphenyl methyl halide into liquid ammonia to obtain N methyl triphenyl ammonia; (b) under the temperature of between 60 DEG C below zero and 70 DEG Cbelow zero, adding n-butyl lithium into organic solution of N methyl triphenyl ammonia to obtain organic solution of N methyl (triphenyl) lithium amide; (c) at the temperature of between 50 DEG C below zero and 70 DEG C below zero, dropwise adding organic solution of (S)-tert-butyl sulfinic acid tert-butyl thioester into the N-methyl (triphenyl) lithium amide, quenching the mixture by using water, carrying out deodorization by using dimethyl sulfate, destroying excessive dimethyl sulfate by using ammonia and carrying out post treatment to obtain (S)-N-methyl (triphenyl) tert-butyl sulfinamide; and (d) taking the product in the step (c), adding dilute acid into the product, adjusting the pH value of the mixture to 3, neutralizing the mixture by using alkaline solution until the pH value isbetween 13 and 14 and carrying out post treatment to obtain (S)-tert-butyl sulfinamide. The process method for synthetizing the tert-butyl sulfinamide has simple and convenient operation and good process stability, avoids copious cooling at the low or ultralow temperature, reduces the using amount of ammonia, removes foul odour and is easy to realize industrial production.

Description

1. Technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing tert-butylsulfinamide. 2. Background technology: [0002] More than 75% of the drugs and drug candidates have ammonia functional groups. Nevertheless, the development of asymmetric ammonia is much later than that of other common functional group asymmetric synthesis. In recent years, tert-butyl sulfinamide has attracted more and more attention and application in asymmetric synthesis. In drug synthesis, tert-butyl sulfinamide is introduced on the aromatic ring, [References: Dembowski, Udo; Noltemeyer , Mathias; Gilje, John W.; Roesky, Herbert W.; CHBEAM; Chem.; 1991, 124, 1917-1922]; 2001, 40, 4544.]. In recent years, there have been literatures on the synthesis of (S)-tert-butylsulfinamide. as follows: [0003] [0004] Use commercially available tetrahydrofuran solution of (S or R)-tert-butylsulfinic acid tert-butylthioester, slow...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C313/06
Inventor 郎丰睿房佳妮李晓王丽杰
Owner DALIAN NETCHEM CHIRAL TECH
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