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Preparation method of N-tert-butyl-4-aminobenzamide

A technology of aminobenzamide and nitrobenzamide, which is applied in the field of preparation of N-tert-butyl-4-aminobenzamide, can solve the problems of low condensation reaction yield, unfriendly environment and the like, and achieves environmental friendliness , the effect of improving yield

Pending Publication Date: 2019-10-08
CHANGZHOU YONGHE FINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The disadvantages of this method are: (1) the condensation reaction yield is low, less than 80%; (2) the reduction reaction requires the use of toxic hydrazine hydrate, which is not friendly to the environment

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0015] The present embodiment is the preparation method of N-tert-butyl-4-nitrobenzamide, specifically as follows:

[0016] Add 260mL of toluene and 100mL of water into a 1L four-necked flask, then add 53.0g of sodium carbonate (0.5mol) while stirring, continue to stir for 10min, cool to 5°C, and add 73.0g of tert-butylamine (1.0mol).

[0017] Add 200mL of toluene solution containing 92.8g p-nitrobenzoyl chloride (0.5mol) dropwise in an ice-water bath at a temperature below 10°C, stir and react at below 10°C (8°C in this example) for 1 hour after dropping, and then at room temperature (This example is at 20° C.) Stir the reaction for 1 h, and finally raise the temperature to reflux, and continue the reaction for 2 h.

[0018] After the reaction, the layers were left to stand, the water layer was removed, the organic layer was cooled and crystallized, filtered with suction, the filter cake was rinsed with 100mL of toluene, dried by suction, and dried at 65°C to obtain 104.0g of...

Embodiment 2～ Embodiment 5）

[0020] The preparation method of each embodiment is basically the same as that of Example 1, and the differences are shown in Table 1.

[0021] Table 1

[0022] Example 1 Example 2 Example 3 Example 4 Example 5 Condensation reaction solvent 260+200mL toluene and 100mL water 380+200mL toluene and 100mL water 260+200mL toluene and 200mL water 260+200mL toluene and 100mL water 260+200mL toluene and 100mL water Condensation reaction temperature and time Reaction at 8°C for 1h, reaction at 20°C for 1h, reaction at reflux for 2h Reaction at 8°C for 1h, reaction at 20°C for 1h, reaction at reflux for 2h Reaction at 8°C for 1h, reaction at 20°C for 1h, reaction at reflux for 2h Reaction at 10°C for 0.5h, reaction at 25°C for 0.5h, reaction at reflux for 3h Reaction at 5°C for 1.5h, reaction at 15°C for 1.5h, reaction at reflux for 1.5h Nitro weight 104.0g 102.3g 102.8g 101.5g 100.0g Condensation reaction yield 93.7% 92.2%...

Embodiment 6）

[0028] Present embodiment is the preparation method of N-tert-butyl-4-aminobenzamide, specifically as follows:

[0029] Put 104.0g of N-tert-butyl-4-nitrobenzamide and 1.5g of 5wt% Pd / C catalyst prepared in step ① into a 2L hydrogenation reactor, first replace it with nitrogen for 3 times, and then replace it with hydrogen Replace 3 times, turn on the heating, after the internal temperature rises to 70°C, the hydrogen absorption speed is obviously accelerated, turn on the cooling water to control the temperature to less than 100°C for reaction, after the hydrogen absorption is completed, continue the heat preservation reaction for 1 hour.

[0030] Filtrate while hot, rinse the filtrate with a small amount of toluene, then cool to below 10°C to crystallize, filter with suction, rinse the filter cake with 50mL of cold toluene, drain, and dry at 65°C to obtain 86.5g of N-tert-butyl -4-aminobenzamide, the yield is 96.2%, and the purity is 99.3%.

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PUM

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Abstract

The invention discloses a preparation method of N-tert-butyl-4-aminobenzamide. The preparation method of the N-tert-butyl-4-aminobenzamide comprises the steps that a condensation reaction is carried out on p-nitrobenzoyl chloride and tert-butylamine to obtain N-tert-butyl-4-nitrobenzamide, and further, the N-tert-butyl-4-aminobenzamide is obtained by catalytic hydrogenation, wherein the condensation reaction is carried out in the presence of a mixed solvent, the mixed solvent is toluene-water, and the condensation reaction comprises the steps that reaction is carried out at 5-10 DEG C for 0.5-2 h, and then reaction is carried out at room temperature for 0.5-2 h, and finally heating is carried out to reflux for reaction for 1-4 h. According to the condensation reaction of the preparation method of the N-tert-butyl-4-aminobenzamide, toluene and water are used as the mixed solvent, then reaction is carried out at room temperature for a certain period of time, and then heating is carried out to reflux to continue the reaction for a certain period of time, so that the yield of the condensation reaction can be significantly increased; and the reduction reaction avoids the use of hydrazine hydrate, and environmental-protection is achieved.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and in particular relates to a preparation method of N-tert-butyl-4-aminobenzamide. Background technique [0002] N-tert-butyl-4-aminobenzamide [English name is N-tert-butyl-4-aminobenzamide, referred to as TBAB; molecular formula is C 11 h 16 N 2 O; molecular weight 192.25754; CAS number 93483-71-7] is an important benzamide compound, which can be used to treat HIV dementia. [0003] At present, there are few literature reports on the preparation method of N-tert-butyl-4-aminobenzamide. [0004] Chinese patent documents CN1182416A and CN1218399A all disclose a kind of preparation method of N-tert-butyl-4-aminobenzamide, comprising the condensation reaction of tert-butylamine and 4-nitrobenzoyl chloride in ethyl acetate to prepare N-tert-butyl Butyl-4-nitrobenzamide, and its reduction to N-tert-butyl-4-aminobenzamide with hydrazine hydrate under Pd / C catalysis. [0005] The disadvanta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/02C07C233/65C07C231/12C07C237/30
CPCC07C231/02C07C231/12C07C233/65C07C237/30
Inventor 姜友林陆海峰宋菊红许晓春陈云峰
Owner CHANGZHOU YONGHE FINE CHEM
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