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Preparing method of N, N-dimethylbenzamide

A technology of dimethylbenzamide and dimethylamine, which is applied to the preparation of carboxylic acid amides, the preparation of organic compounds, chemical instruments and methods, etc., and can solve the problem of harsh preparation and storage conditions and hydrogenation process of dimethylamine lithium salt Problems such as poor operation safety and difficult preparation of raw materials have achieved the effect of cheap and easy-to-obtain raw materials, high safety and simple operation

Active Publication Date: 2009-11-25
NUTRICHEM LAB CO LTD
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Problems solved by technology

[0006] 2. The literature (Tetrahedron Letters, 1992, 33 (43): 6453-6456) records the method for preparing o-amino-N, N-dimethylbenzamide from anthranilate and dimethylamine lithium salt, But the preparation and storage conditions of dimethylamine lithium salt in this route are harsher;
[0008] 3. Literature (Pesticide Science, 1996, 46: 151-156) records the preparation of o-amino-N, N-dimethylbenzamide by rearrangement reaction of 1,1-dimethylamino-3-phenylurea Method, but the raw material of this reaction is not easy to prepare;
[0010] 4. Documents (Journal of the Chemical Society, PT1, 1995, 11: 1349-1358; Journal of Medicinal Chemistry, 1997, 40: 2674-2687) and patents (US5985837, US5688795, US20080182852, etc.) The method for preparing o-amino-N, N-dimethylbenzamide by hydrogenation reduction of N, N-dimethylbenzamide, the reaction yield of this method is high, but the raw materials are expensive, and the safety of the hydrogenation process operation is poor

Method used

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  • Preparing method of N, N-dimethylbenzamide

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Embodiment 1

[0020] Embodiment 1 o-amino-N, the preparation of N-dimethylbenzamide

[0021] Take 82.3g (0.5mol, 99.0%) of isatoic anhydride in a reaction flask, add 400mL of methanol, start stirring, cool down to below -10°C with frozen brine, and then introduce 34g (0.75mol, 99.9%) of dimethylamine gas . Subsequently, it was returned to room temperature, and the reaction was stirred for 4 hours. Negative pressure precipitation yielded 80.5 g of the target compound o-amino-N,N-dimethylbenzamide with a purity of 98.8% and a yield of 96.8%.

Embodiment 2

[0022] Embodiment 2 o-amino-N, the preparation of N-dimethylbenzamide

[0023] Take 82.3g (0.5mol, 99.0%) of isatoic anhydride in a reaction flask, add 400mL of dichloroethane, start stirring, cool down to below 10°C with frozen brine, then add 68g (0.6mol, 40%) of dimethyl Amine solution. Subsequently, it was returned to room temperature, and the reaction was stirred for 5 hours. Separate the layers, extract the aqueous phase once with dichloroethane, combine the organic phases, and precipitate under negative pressure to obtain 74.2 g of the target compound o-amino-N, N-dimethylbenzamide, with a purity of 94.0% and a yield of 85.0 %.

Embodiment 3

[0024] Embodiment 3 o-amino-N, the preparation of N-dimethylbenzamide

[0025] Take 82.3g (0.5mol, 99.0%) of isatoic anhydride in a reaction flask, add 400mL of acetonitrile, start stirring, cool down to below 10°C with frozen brine, then add 62g (0.55mol, 40%) of dimethylamine aqueous solution. Subsequently, it was returned to room temperature, and the reaction was stirred for 4 hours. Negative pressure precipitation yielded 77.8 g of the target compound o-amino-N,N-dimethylbenzamide with a purity of 96.5% and a yield of 91.6%.

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Abstract

The invention relates to a preparing method of o-amino N, N-dimethylbenzamide, which is prepared by reacting isatoic anhydride and dimethylamine or dimethylamino aminic acid. The method has advantages of easy-obtained and cheap production raw materials, high reaction yield, simple operation and easy industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of o-amino-N,N-dimethylbenzamide. Background technique [0002] O-amino-N,N-dimethylbenzamide is an important intermediate in the preparation of sulfonylurea herbicide Orthosulfamuron and certain pharmaceutical products. [0003] Existing document reports o-amino-N, the preparation method of N-dimethylbenzamide mainly contains following four kinds: [0004] 1. The literature (Tetrahedron, 1970, 26:2007-2026) records the method for preparing o-amino-N, N-dimethylbenzamide by reacting anthranilyl chloride and dimethylamine, but due to anthranilic acid The acid chloride itself will react, resulting in poor reaction selectivity and low yield; [0005] [0006] 2. The literature (Tetrahedron Letters, 1992, 33 (43): 6453-6456) records the method for preparing o-amino-N, N-dimethylbenzamide from anthranilate and dimethylamine lithium salt, But the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/30C07C231/10
Inventor 王文军罗世英荆呈峰刘世禄曹锦母灿先
Owner NUTRICHEM LAB CO LTD
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