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Synthesis method of sulfonyl carbamate

A technology of sulfone carbamate and ethyl carbamate, which is applied in the field of chemical intermediate preparation, can solve the problems of difficulty in synthesizing sulfone carbamate, high limitations, high toxicity of raw materials, etc., and achieves stable catalytic effect, Simple operation and ideal yield

Active Publication Date: 2021-09-03
SUZHOU HUADAO BIOLOGICAL PHARMA
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  • Description
  • Claims
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Problems solved by technology

[0007] Existing sulfone carbamates are based on I 2 / DMSO is the reaction medium, and it is prepared by reacting p-toluenesulfonylmethyl isocyanide and alcohol as raw materials [Synlett 2018, 29(15):2039-2042.]; the method is fast and effective, and the reaction conditions are mild, but it needs Prepared from arylsulfonylmethyl isocyanide; this raw material has high toxicity and high limitations, and it is difficult to synthesize various types of sulfone carbamates, which cannot meet the needs of various synthesis

Method used

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  • Synthesis method of sulfonyl carbamate
  • Synthesis method of sulfonyl carbamate
  • Synthesis method of sulfonyl carbamate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: the synthesis of N-[(4-methylbenzenesulfonyl) methyl] ethyl carbamate

[0039]

[0040] Put 18 grams of urethane, 9 grams of paraformaldehyde, 40 grams of sodium p-toluene sulfinate, 1 gram of copper oxide and 150 milliliters of water into a 500 mL miniature autoclave, stir evenly, and use high-purity oxygen to replace 3 The second time, the reactor was closed, the temperature was gradually raised to 120° C., and the reaction was kept for 2 hours.

[0041] Cool to room temperature, extract twice with ethyl acetate, combine the organic phases, wash three times with water, then dry over anhydrous sodium sulfate, filter, concentrate to remove the organic solvent, and recrystallize the residue with ethanol to obtain 47.3 g of the product, liquid phase Purity 99.8%; 1 H (NMR, CDCl 3 ): 7.78 (d, J=8.4Hz, 2H), 7.35 (d, J=8.4Hz, 2H), 5.53 (brs, 1H), 4.56 (d, J=6.8Hz, 2H), 3.98 (q, J =7.2Hz, 2H), 2.45(s, 3H), 1.14(t, J=7.2Hz, 3H).

Embodiment 2

[0042] Embodiment 2: the synthesis of N-[(4-methylbenzenesulfonyl) methyl] ethyl carbamate

[0043]

[0044] Put 18 grams of urethane, 9 grams of paraformaldehyde, 40 grams of sodium p-toluene sulfinate, 2 grams of cuprous chloride and 150 milliliters of water into a 500 mL miniature autoclave. After stirring evenly, use high-purity oxygen Replaced 3 times, closed the reactor, gradually raised the temperature to 120°C, and kept the reaction for 1 hour.

[0045] Cool to room temperature, filter with suction, wash the solid with water until it becomes colorless, and recrystallize the residue with ethanol to obtain 48.2 g of the product with a liquid phase purity of 99.8%.

Embodiment 3

[0046]Embodiment 3: the synthesis of N-[(benzenesulfonyl) methyl] ethyl carbamate

[0047]

[0048] Put 18 grams of urethane, 8 grams of paraformaldehyde, 35 grams of sodium benzene sulfinate, 2 grams of tetraammine copper acetate and 100 milliliters of water into a 500 mL miniature autoclave. After stirring evenly, use high-purity oxygen Replaced 3 times, closed the reactor, gradually raised the temperature to 90°C, and kept the reaction for 1 hour.

[0049] Cool to room temperature, filter with suction, wash the solid with water until it becomes colorless, and recrystallize the residue with ethanol to obtain 49.5 g of the product, with a liquid phase purity of 99.6%; 1 H (NMR, CDCl 3 ): 7.96-7.94 (m, 2H), 7.69-7.65 (m, 1H), 7.60-7.57 (m, 2H), 5.51 (brs, 1H), 4.55 (d, J=6.8Hz, 2H), 3.99 ( q, J = 7.2Hz, 2H), 2.44 (s, 3H), 1.15 (t, J = 7.2Hz, 3H).

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Abstract

The invention discloses a synthesis method of sulfuryl carbamate, and the method comprises the following steps: by taking sodium aromatic sulfinate, ethyl carbamate and paraformaldehyde as reaction raw materials, carrying out catalytic reaction under the action of a reaction catalyst and under the conditions of heating and pressurizing to prepare the sulfuryl carbamate. The synthesis method is easy and convenient to operate and low in production cost, the adopted synthesis raw materials are low in price, easy to obtain, non-toxic, green and environmentally friendly, the obtained target product is high in purity and ideal in yield, and large-scale production of the sulfuryl carbamate can be achieved.

Description

technical field [0001] The invention belongs to the technical field of preparation of chemical intermediates, in particular to a method for synthesizing sulfone carbamate. Background technique [0002] Carbamate compounds are a class of nitrogen-containing compounds with important biological and pharmaceutical activities, and are widely used in agriculture, medical and health fields. Insecticides, acaricides, herbicides and fungicides widely used in agricultural production, such as Yechansan, Carbofuran, Benomyl, and Avenate all belong to carbamate pesticides. In medicine, the drug darunavir for the treatment of AIDS and the drug solifenacin succinate for the treatment of bladder spasm are also carbamate compounds; in addition, carbamate is the basic skeleton and important synthetic intermediate of many natural products and chemical raw materials. [0003] Usually, the synthesis of carbamate compound mainly adopts following three methods: (1) utilize chloroformate and ammo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/00C07C317/28
CPCC07C315/00C07C317/28
Inventor 陆军刘辉于锡东左美娟刘明荣
Owner SUZHOU HUADAO BIOLOGICAL PHARMA
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