CN102531888A - Chemical synthesis method of 3,4,5-trimethoxy benzoyl chloride - Google Patents
Chemical synthesis method of 3,4,5-trimethoxy benzoyl chloride Download PDFInfo
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Abstract
The invention discloses a chemical synthesis method of 3,4,5-trimethoxy benzoyl chloride. In the synthesis method, the 3,4,5-trimethoxy benzoyl chloride is prepared by taking 3,4,5- trimethoxybenzoic acid and bis(trichloromethyl)carbonate as raw materials and fully reacting in an organic solvent under the action of an organic amine catalyst at the temperature of 20-70 DEG C. The synthesis method has the advantages of reasonable process, low production cost, high reaction yield and good product quality, and is suitable for industrial production.
Description
(1) technical field
The present invention relates to a kind of gastrointestinal antispasmodic medicine Trimebutine Maleate key intermediate 3,4, the compound method of 5-trimethoxy-benzoyl chloride.
(2) background technology
3,4, the 5-trimethoxy-benzoyl chloride is the key intermediate of synthetic Trimebutine Maleate; Trimebutine Maleate is a kind of amino ester compound that the Jouveinal company of France develops; Belong to the gastrointestinal tract dynamia medicine, 1970 first in France listing, goes on the market in China in 2000; Got into national medical insurance catalogue in 2004.
Before the present invention provided, in the prior art 3,4, mostly the compound method of 5-trimethoxy-benzoyl chloride was that with 3,4 the chlorination of 5-trimethoxybenzoic acid and sulfur oxychloride prepares.Like " Heilungkiang medical science " 1998,21 (3): propose following technology among the 48-49: 3,4,5-trimethoxybenzoic acid 30g (0.14mol) adds in the YLENE of 140g, the normal pressure dehydration.After steaming 50mL, add aluminum trichloride (anhydrous) 0.15g (0.001mol) again, be incubated 80 ℃, dripping thionyl chloride 16.6g (0.14mol) slowly in 3h.Drip and finish, be warming up to 85 ℃, make 3,4, the 5-trimethoxy-benzoyl chloride behind the reaction 2h.
Contain a large amount of asphyxiant sulfurous gas in the sulfur oxychloride process tail gas, sulphur dioxide emission are national environmental protection to one of six indexs of a control of atmosphere, three wastes difficult treatment, and expense is high.The transportation of sulfur oxychloride and use receive strict control in addition, and be high to the sealing requirements of conversion unit, and investment is also than shortcomings such as big and production security differences.
Prepare in the reaction of acyl chlorides at many carboxylic acids at present, use two (trichloromethyl) carbonic ethers to substitute sulfur oxychloride gradually as chlorination reagent.Common that method for making is under the catalysis of organic amine, the carboxylic acid chlorination to be generated acyl chlorides.But we find in experiment; Using two (trichloromethyl) carbonic ethers as 3,4 of chlorination reagent, 5-trimethoxybenzoic acid synthetic 3; 4; In the reaction of 5-trimethoxy-benzoyl chloride, adopt conventional like organic amines such as triethylamine, DMF during as catalyzer reaction yield lower, be inappropriate for suitability for industrialized production.
Therefore industrial unfavorable factor more than being directed against is necessary existing processes is improved.
(3) summary of the invention
The technical problem that the present invention will solve provides that a kind of technology is reasonable, production cost is low, reaction yield is high, 3,4 of good product quality, the chemical synthesis process of 5-trimethoxy-benzoyl chloride.
For solving the problems of the technologies described above, the technical scheme that the present invention adopts is following:
A kind of 3,4, the chemical synthesis process of 5-trimethoxy-benzoyl chloride; Said compound method is with 3,4, and the 5-trimethoxybenzoic acid is a raw material with two (trichloromethyl) carbonic ethers; In organic solvent, under the organic amine catalyst action, fully react in 20～70 ℃; Make described 3,4, the 5-trimethoxy-benzoyl chloride; Reaction equation is as follows:
It is one of following that described organic amine catalyzer is selected from: three (2-cyano methyl) amine, three (2-cyano ethyl) amine, three (2-cyanic acid propyl group) amine, N, N, N '; N '-four (3-cyano methyl) quadrol, N, N, N ', N '-four (3-cyano ethyl) quadrol, N; N, N ', N '-four (3-cyanic acid propyl group) quadrol, N, N-two (3-cyano methyl) benzylamine; N, N-two (3-cyano ethyl) benzylamine, N, N-two (3-cyanic acid propyl group) benzylamine, N-(3-cyanic acid propyl group) benzylamine;
It is one of following that described reaction solvent is selected from: toluene, YLENE, methylene dichloride, tetracol phenixin, 1,2-ethylene dichloride, 1,4-dioxane, ETHYLE ACETATE, normal hexane, THF, 2-methyltetrahydrofuran, acetonitrile.
Among the present invention; Described 3,4, the ratio of the amount of substance that feeds intake of 5-trimethoxybenzoic acid, two (trichloromethyl) carbonic ether, organic amine is 1: 0.33～3.0: 0.03～3.0; Preferred 1: 0.33～1.0: 0.05～0.3, more preferably 1: 0.33～0.5: 0.1～0.2.
Among the present invention, the quality consumption of said reaction solvent is 3,4,1～20 times of 5-trimethoxybenzoic acid, preferred 5～20 times, more preferably 10～20 times.
Further, the preferred N of described organic amine catalyzer, N, N ', N '-four (3-cyanic acid propyl group) quadrol or three (2-cyano ethyl) amine, more preferably N, N, N ', N '-four (3-cyanic acid propyl group) quadrol.
Further, described reaction solvent is preferably methylene dichloride, THF or 2-methyltetrahydrofuran, more preferably 2-methyltetrahydrofuran.
Reaction according to the invention, the reaction times is preferably 4～10 hours; Temperature of reaction is preferably 50～70 ℃.
The present invention is concrete to recommend described chemical synthesis process to carry out according to following steps: with 3,4,5-trimethoxybenzoic acid and organic amine are dissolved in the organic solvent; 20～70 ℃ of two (trichloromethyl) carbonate solutions that stir down and drip with organic solvent dissolution; Dropwise back insulation reaction 4～10h, reaction finishes the back and reclaims organic solvent, and residual solids gets described 3 through recrystallization; 4, the 5-trimethoxy-benzoyl chloride.Described 3,4, the ratio of the amount of substance that feeds intake of 5-trimethoxybenzoic acid, two (trichloromethyl) carbonic ether, organic amine is 1: 0.33～1.0: 0.03～0.1; Described organic solvent is the 2-methyltetrahydrofuran; Described organic amine catalyzer is N, N, N ', N '-four (3-cyanic acid propyl group) quadrol; The quality consumption of said 2-methyltetrahydrofuran is 3,4,5～20 times of 5-trimethoxybenzoic acid quality; Described recrystallization solvent is with dry sherwood oil or the hexanaphthene of crossing of calcium chloride.
Compared with prior art, the present invention is a chlorination reagent with two (trichloromethyl) carbonic ether, through selecting suitable organic amine catalyzer and cooperating suitable reaction solvent; Reaction generates 3; 4, the 5-trimethoxy-benzoyl chloride has that equipment corrosion is little, production cost is low, reaction conditions is gentle, safety simple to operate, the three wastes are few and easy processing, advantage such as product yield is high, quality is good; Avoided to water and air responsive the use of aluminum chloride, be a kind of novel method of suitable suitability for industrialized production.
So compound method of the present invention has bigger implementary value and economic results in society.
(4) embodiment
Below in conjunction with embodiment technical scheme of the present invention is described further, but protection scope of the present invention is not limited to this.
Embodiment 1
Feed intake amount of substance than 3,4, the 5-trimethoxybenzoic acid: two (trichloromethyl) carbonic ether: the organic amine catalyzer is to feed intake at 1: 0.33: 0.1,3,4, and 5-trimethoxybenzoic acid 21.2g (0.1mol); Two (trichloromethyl) carbonic ether 9.8g (0.033mol); The organic amine catalyzer is N, N, N ', N '-four (3-cyanic acid propyl group) quadrol, the quality that feeds intake 3.28g (0.01mol); Organic solvent is THF 212g, and its total consumption is 3,4,10 times of 5-trimethoxybenzoic acid quality.
With 3,4,5-trimethoxybenzoic acid and organic amine are dissolved in organic solvent (consumption of organic solvent is 3,4,5-trimethoxybenzoic acid quality 7 times).Will two (trichloromethyl) carbonic ethers be dissolved in organic solvent (consumption of organic solvent is 3,4,5-trimethoxybenzoic acid quality 3 times); Slowly drop to 3,4, in the solution of 5-trimethoxybenzoic acid and organic amine; Temperature of reaction is 70 ℃, 5 afterreaction end as a child.
Reaction finishes the back underpressure distillation and reclaims organic solvent, remain in the reaction flask solid through with calcium chloride dry the sherwood oil recrystallization get white solid, promptly 3,4,5-trimethoxy-benzoyl chloride 20.2g, yield 88%, purity 98.7%.
Nuclear magnetic resonance spectrum (Bruke):
1H NMR (CDCl
3, 500MHz): δ (ppm)=3.91 (6H, s), 3.92 (3H, s), 7.36 (2H, s);
13C NMR (CDCl
3, 125MHz): δ (ppm)=56.2,60.9,107.4,124.1,142.9,152.9,171.8.
Embodiment 2
Feed intake amount of substance than 3,4, the 5-trimethoxybenzoic acid: two (trichloromethyl) carbonic ether: the organic amine catalyzer is to feed intake at 1: 0.33: 0.1,3,4, and 5-trimethoxybenzoic acid 21.2g (0.1mol); Two (trichloromethyl) carbonic ether 9.8g (0.033mol); The organic amine catalyzer is N, N, N ', N '-four (3-cyanic acid propyl group) quadrol, the quality that feeds intake 3.28g (0.01mol); Organic solvent is THF 212g, and its total consumption is 3,4,10 times of 5-trimethoxybenzoic acid quality.
Temperature of reaction is 70 ℃, and in 8 hours reaction times, other is operated with instance 1,3,4,5-trimethoxy-benzoyl chloride 18.9g, yield 82%, purity 99.0%.
Embodiment 3
Feed intake amount of substance than 3,4, the 5-trimethoxybenzoic acid: two (trichloromethyl) carbonic ether: the organic amine catalyzer is to feed intake at 1: 0.5: 0.1,3,4, and 5-trimethoxybenzoic acid 21.2g (0.1mol); Two (trichloromethyl) carbonic ether 14.85g (0.05mol); The organic amine catalyzer is three (2-cyano ethyl) amine, the quality that feeds intake 1.76g (0.01mol); Organic solvent is 2-methyltetrahydrofuran 212g, and its total consumption is 3,4,10 times of 5-trimethoxybenzoic acid quality.
Temperature of reaction is 70 ℃, and in 8 hours reaction times, other is operated with instance 1,3,4,5-trimethoxy-benzoyl chloride 17.9g, yield 78%, purity 99.2%.
Embodiment 4
Feed intake amount of substance than 3,4, the 5-trimethoxybenzoic acid: two (trichloromethyl) carbonic ether: the organic amine catalyzer is to feed intake at 1: 0.5: 0.1,3,4, and 5-trimethoxybenzoic acid 21.2g (0.1mol); Two (trichloromethyl) carbonic ether 14.85g (0.05mol); The organic amine catalyzer is N, N, N ', N '-four (3-cyanic acid propyl group) quadrol, the quality that feeds intake 3.28g (0.01mol); Organic solvent is methylene dichloride 212g, and its total consumption is 3,4,10 times of 5-trimethoxybenzoic acid quality.
Temperature of reaction is 40 ℃, and in 10 hours reaction times, other is operated with instance 1,3,4,5-trimethoxy-benzoyl chloride 16.3g, yield 71%, purity 98.6%.
Embodiment 5
Feed intake amount of substance than 3,4, the 5-trimethoxybenzoic acid: two (trichloromethyl) carbonic ether: the organic amine catalyzer is to feed intake at 1: 0.33: 0.05,3,4, and 5-trimethoxybenzoic acid 21.2g (0.1mol); Two (trichloromethyl) carbonic ether 9.8g (0.033mol); The organic amine catalyzer is N, N, N ', N '-four (3-cyanic acid propyl group) quadrol, the quality that feeds intake 1.64g (0.005mol); Organic solvent is 2-methyltetrahydrofuran 212g, and its total consumption is 3,4,8 times of 5-trimethoxybenzoic acid quality.
Temperature of reaction is 50 ℃, and in 7 hours reaction times, other is operated with instance 1,3,4,5-trimethoxy-benzoyl chloride 15.9g, yield 69%, purity 98.8%.
Embodiment 6
Feed intake amount of substance than 3,4, the 5-trimethoxybenzoic acid: two (trichloromethyl) carbonic ether: the organic amine catalyzer is to feed intake at 1: 0.33: 0.2,3,4, and 5-trimethoxybenzoic acid 21.2g (0.1mol); Two (trichloromethyl) carbonic ether 9.8g (0.033mol); The organic amine catalyzer is N, N, N ', N '-four (3-cyanic acid propyl group) quadrol, the quality that feeds intake 6.56g (0.02mol); Organic solvent is 2-methyltetrahydrofuran 212g, and its total consumption is 3,4,15 times of 5-trimethoxybenzoic acid quality.
Temperature of reaction is 70 ℃, and in 9 hours reaction times, other is operated with instance 1,3,4,5-trimethoxy-benzoyl chloride 19.8g, yield 86%, purity 99.0%.
Embodiment 7
Feed intake amount of substance than 3,4, the 5-trimethoxybenzoic acid: two (trichloromethyl) carbonic ether: the organic amine catalyzer is to feed intake at 1: 0.5: 0.1,3,4, and 5-trimethoxybenzoic acid 21.2g (0.1mol); Two (trichloromethyl) carbonic ether 14.85g (0.05mol); The organic amine catalyzer is N, N, N ', N '-four (3-cyanic acid propyl group) quadrol, the quality that feeds intake 3.28g (0.01mol); Organic solvent is 2-methyltetrahydrofuran 212g, and its total consumption is 3,4,10 times of 5-trimethoxybenzoic acid quality.
Temperature of reaction is 50 ℃, and in 4 hours reaction times, other is operated with instance 1,3,4,5-trimethoxy-benzoyl chloride 18.6g, yield 81%, purity 98.9%.
Embodiment 8
Feed intake amount of substance than 3,4, the 5-trimethoxybenzoic acid: two (trichloromethyl) carbonic ether: the organic amine catalyzer is to feed intake at 1: 0.5: 0.1,3,4, and 5-trimethoxybenzoic acid 21.2g (0.1mol); Two (trichloromethyl) carbonic ether 14.85g (0.05mol); The organic amine catalyzer is N, N, N ', N '-four (3-cyanic acid propyl group) quadrol, the quality that feeds intake 3.28g (0.01mol); Organic solvent is 2-methyltetrahydrofuran 212g, and its total consumption is 3,4,10 times of 5-trimethoxybenzoic acid quality.
Temperature of reaction is 40 ℃, and in 8 hours reaction times, other is operated with instance 1,3,4,5-trimethoxy-benzoyl chloride 14.4g, yield 68%, purity 97.9%.
Embodiment 9
Feed intake amount of substance than 3,4, the 5-trimethoxybenzoic acid: two (trichloromethyl) carbonic ether: the organic amine catalyzer is to feed intake at 1: 0.5: 0.1,3,4, and 5-trimethoxybenzoic acid 21.2g (0.1mol); Two (trichloromethyl) carbonic ether 14.85g (0.05mol); The organic amine catalyzer is N, N-two (3-cyanic acid propyl group) benzylamine, the quality that feeds intake 2.41g (0.01mol); Organic solvent is 2-methyltetrahydrofuran 212g, and its total consumption is 3,4,10 times of 5-trimethoxybenzoic acid quality.
Temperature of reaction is 70 ℃, and in 6 hours reaction times, other is operated with instance 1,3,4,5-trimethoxy-benzoyl chloride 16.2g, yield 70%, purity 98.6%.
Embodiment 10
Feed intake amount of substance than 3,4, the 5-trimethoxybenzoic acid: two (trichloromethyl) carbonic ether: the organic amine catalyzer is to feed intake at 1: 0.5: 0.1,3,4, and 5-trimethoxybenzoic acid 21.2g (0.1mol); Two (trichloromethyl) carbonic ether 14.85g (0.05mol); The organic amine catalyzer is N, N-two (3-cyanic acid propyl group) benzylamine, the quality that feeds intake 2.27g (0.01mol); Organic solvent is 2-methyltetrahydrofuran 212g, and its total consumption is 3,4,10 times of 5-trimethoxybenzoic acid quality.
Temperature of reaction is 70 ℃, and in 10 hours reaction times, other is operated with instance 1,3,4,5-trimethoxy-benzoyl chloride 14.6g, yield 63%, purity 99.2%.
The comparative example 1
Feed intake amount of substance than 3,4, the 5-trimethoxybenzoic acid: two (trichloromethyl) carbonic ether: the organic amine catalyzer is to feed intake at 1: 0.5: 0.05,3,4, and 5-trimethoxybenzoic acid 21.2g (0.1mol); Two (trichloromethyl) carbonic ether 14.85g (0.05mol); The organic amine catalyzer is 1,3-dimethyl--2-imidazolidone, the quality that feeds intake 0.57g (0.05mol); Organic solvent is methylene dichloride 318g, and its total consumption is 3,4,15 times of 5-trimethoxybenzoic acid quality.
Temperature of reaction is 30 ℃, and in 15 hours reaction times, other is operated with instance 1,3,4,5-trimethoxy-benzoyl chloride 13.1g, yield 57%, purity 98.6%.
The comparative example 2
Feed intake amount of substance than 3,4, the 5-trimethoxybenzoic acid: two (trichloromethyl) carbonic ether: the organic amine catalyzer is to feed intake at 1: 0.33: 0.1,3,4, and 5-trimethoxybenzoic acid 21.2g (0.1mol); Two (trichloromethyl) carbonic ether 9.8g (0.033mol); The organic amine catalyzer is a triethylamine, the quality that feeds intake 1.01g (0.01mol); Organic solvent is THF 212g, and its total consumption is 3,4,10 times of 5-trimethoxybenzoic acid quality.
Temperature of reaction is 70 ℃, and in 5 hours reaction times, other is operated with instance 1,3,4,5-trimethoxy-benzoyl chloride 11.7g, yield 51%, purity 98.4%.
The comparative example 3
Feed intake amount of substance than 3,4, the 5-trimethoxybenzoic acid: two (trichloromethyl) carbonic ether: the organic amine catalyzer is to feed intake at 1: 0.33: 0.1,3,4, and 5-trimethoxybenzoic acid 21.2g (0.1mol); Two (trichloromethyl) carbonic ether 9.8g (0.033mol); The organic amine catalyzer is N, dinethylformamide, the quality that feeds intake 0.73g (0.01mol); Organic solvent is THF 212g, and its total consumption is 3,4,10 times of 5-trimethoxybenzoic acid quality.
Temperature of reaction is 70 ℃, and in 8 hours reaction times, other is operated with instance 1,3,4,5-trimethoxy-benzoyl chloride 10.8g, yield 47%, purity 98.3%.
The comparative example 4
Feed intake amount of substance than 3,4, the 5-trimethoxybenzoic acid: two (trichloromethyl) carbonic ether: the organic amine catalyzer is to feed intake at 1: 0.5: 0.05,3,4, and 5-trimethoxybenzoic acid 21.2g (0.1mol); Two (trichloromethyl) carbonic ether 14.85g (0.05mol); The organic amine catalyzer is N, N, N ', N '-four (3-cyanic acid propyl group) quadrol, the quality that feeds intake 3.28g (0.01mol); Organic solvent is methylene dichloride 318g, and its total consumption is 3,4,10 times of 5-trimethoxybenzoic acid quality.
Temperature of reaction is 90 ℃, and in 2 hours reaction times, other is operated with instance 1,3,4,5-trimethoxy-benzoyl chloride 10.6g, yield 46%, purity 98.6%.
Claims (10)
1. one kind 3,4, the chemical synthesis process of 5-trimethoxy-benzoyl chloride; It is characterized in that: said compound method is with 3,4, and the 5-trimethoxybenzoic acid is a raw material with two (trichloromethyl) carbonic ethers; In organic solvent, under the organic amine catalyst action, fully react in 20～70 ℃; Make described 3,4, the 5-trimethoxy-benzoyl chloride;
It is one of following that described organic amine catalyzer is selected from: three (2-cyano methyl) amine, three (2-cyano ethyl) amine, three (2-cyanic acid propyl group) amine, N, N, N '; N '-four (3-cyano methyl) quadrol, N, N, N ', N '-four (3-cyano ethyl) quadrol, N; N, N ', N '-four (3-cyanic acid propyl group) quadrol, N, N-two (3-cyano methyl) benzylamine; N, N-two (3-cyano ethyl) benzylamine, N, N-two (3-cyanic acid propyl group) benzylamine, N-(3-cyanic acid propyl group) benzylamine;
It is one of following that described reaction solvent is selected from: toluene, YLENE, methylene dichloride, tetracol phenixin, 1,2-ethylene dichloride, 1,4-dioxane, ETHYLE ACETATE, normal hexane, THF, 2-methyltetrahydrofuran, acetonitrile.
2. as claimed in claim 13; 4, the chemical synthesis process of 5-trimethoxy-benzoyl chloride is characterized in that: described 3; 4, the ratio of the amount of substance that feeds intake of 5-trimethoxybenzoic acid, two (trichloromethyl) carbonic ether, organic amine is 1: 0.33～1.0: 0.05～0.3; The quality consumption of said reaction solvent is 3,4,5～20 times of 5-trimethoxybenzoic acid.
3. as claimed in claim 13; 4, the chemical synthesis process of 5-trimethoxy-benzoyl chloride is characterized in that: described 3; 4, the ratio of the amount of substance that feeds intake of 5-trimethoxybenzoic acid, two (trichloromethyl) carbonic ether, organic amine is 1: 0.33～0.5: 0.1～0.2; The quality consumption of said reaction solvent is 3,4,10～20 times of 5-trimethoxybenzoic acid.
4. described 3,4 like one of claim 1～3, the chemical synthesis process of 5-trimethoxy-benzoyl chloride is characterized in that: described organic amine catalyst n, N, N ', N '-four (3-cyanic acid propyl group) quadrol or three (2-cyano ethyl) amine.
5. as claimed in claim 43,4, the chemical synthesis process of 5-trimethoxy-benzoyl chloride is characterized in that: described reaction solvent is methylene dichloride, THF or 2-methyltetrahydrofuran.
6. described 3,4 like one of claim 1～3, the chemical synthesis process of 5-trimethoxy-benzoyl chloride is characterized in that: described organic amine catalyst n, and N, N ', N '-four (3-cyanic acid propyl group) quadrol, described reaction solvent is the 2-methyltetrahydrofuran.
7. described 3,4 like one of claim 1～3, the chemical synthesis process of 5-trimethoxy-benzoyl chloride is characterized in that: the reaction times is 4～10 hours.
8. as claimed in claim 73,4, the chemical synthesis process of 5-trimethoxy-benzoyl chloride is characterized in that: temperature of reaction is 50～70 ℃.
9. as claimed in claim 83; 4, the chemical synthesis process of 5-trimethoxy-benzoyl chloride is characterized in that: described organic amine catalyst n; N; N ', N '-four (3-cyanic acid propyl group) quadrol or three (2-cyano ethyl) amine, described reaction solvent is methylene dichloride, THF or 2-methyltetrahydrofuran.
10. as claimed in claim 83; 4, the chemical synthesis process of 5-trimethoxy-benzoyl chloride is characterized in that: described 3; 4, the ratio of the amount of substance that feeds intake of 5-trimethoxybenzoic acid, two (trichloromethyl) carbonic ether, organic amine is 1: 0.33～0.5: 0.1～0.2; Described organic amine catalyst n, N, N ', N '-four (3-cyanic acid propyl group) quadrol; Described reaction solvent is the 2-methyltetrahydrofuran.
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| CN107793312A (en) * | 2016-08-31 | 2018-03-13 | 江苏万隆科技有限公司 | The preparation method of 2,3,4,5 tetrachloro chlorobenzoyl chlorides |
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