CN101565417A - Benzenesulfonyl carboxamide and preparation method thereof - Google Patents
Benzenesulfonyl carboxamide and preparation method thereof Download PDFInfo
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- CN101565417A CN101565417A CNA2009100523713A CN200910052371A CN101565417A CN 101565417 A CN101565417 A CN 101565417A CN A2009100523713 A CNA2009100523713 A CN A2009100523713A CN 200910052371 A CN200910052371 A CN 200910052371A CN 101565417 A CN101565417 A CN 101565417A
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Abstract
The invention discloses a benzenesulfonyl carboxamide and a preparation method thereof, the benzenesulfonyl carboxamide has a structure shown on the right, and the preparation method thereof comprises the steps of: taking 1-[(6-chlorine-3-pyridine)methyl]-2-imidazolone and benzene sulfonyl chloride as raw materials and taking organic amine as catalyst to react for 0.5 to 48 hours at a temperature ranging from 40 to 150 DEG C to prepare the medical lead compound of the benzenesulfonyl carboxamide. The benzenesulfonyl carboxamide and the preparation method thereof have the advantages that the raw materials are easy to obtain and have low cost and hypertoxic reaction raw materials are not used, thereby avoiding severe environmental pollution. The benzenesulfonyl carboxamide and the preparation method thereof are a novel greening process and have good industrial application prospect.
Description
Technical field
The present invention relates to the chemical preparation technical field, specifically a kind of benzenesulfonyl carboxamide and preparation method thereof.
Background technology
Find that sulfonyl urea compound is a class highy potent herbicide seventies in 20th century, be widely used in preventing and treating width leaf weed and gramineous weeds.At present, existing many companies have developed this product, metsulfuronmethyl as E.I.Du Pont Company, chlorine sulphur is grand, the triasulfuron and the primisulfuronmethyl of chlorimuronethyl and sulfometuron-methyl and the exploitation of Ciba-Geigy company, present commercial sulfonylurea herbicide is kind more than 20 nearly, and the sales volume of global annual sulfonylurea herbicide reaches multi-million dollar, account for the weedicide market share and surpass 10%, in agricultural chemicals market, the world, occupy critical role.Sulfonyl urea compound also is widely applied in the pharmaceutical industries simultaneously, be used as a kind of good medicine for the treatment of diabetes, commonly used have tolbutamide (toLbutamid, a D860, tolbutamide), P-607 (chLorpropamide), Glyburide (gLyburide, gLibencLamide, glyburide), Glipizide (gLipizide, Mitoneu), gliclazide (gLicLazipe, diamicron) etc.The sulfonyl urea compound synthetic method mainly is with fragrant heterocyclic sulfonamide and phosgene, oxalyl chloride, sulphonate, chloro-formic ester reaction generates isocyanic ester, then with PYRIMITHAMINE (or atrazin) condensation, generate sulfonylurea.These synthetic methods are at many patents and bibliographical information.
Yet, in these bibliographical informations, mostly used the phosgene synthesis method, the technical requirements complexity, the cost of equipment height needs special security device in industrial production, and this brings certain restriction for the production of sulfonylurea herbicide.Therefore, alternative, effective, inexpensive new herbicides and the new synthetic method of exploitation is noticeable all the time.
Summary of the invention
The object of the invention is to provide a kind of benzenesulfonyl carboxamide and preparation method thereof, use 1-[(6-chloro-3-pyridine) methyl]-2-imidazolone and benzene sulfonyl chloride be raw material, benzenesulfonyl carboxamide agricultural chemicals, medical lead compound have been synthesized by one-step synthesis, step is simple, post-reaction treatment is convenient, productive rate can reach more than 80%, has better industrial application prospect.
The object of the present invention is achieved like this:
Benzenesulfonyl carboxamide provided by the invention is represented with general formula (I):
In the general formula (I):
R is: hydrogen, halogen, C1-C10 alkyl, methoxyl group, nitro, trifluoromethyl or aldehyde radical;
In general formula (I): the alkyl of the preferred hydrogen of R, halogen, nitro or C1-C10;
The alkyl of indication mainly is a methyl in general formula (I), and halogen comprises fluorine, chlorine and bromine.
The preparation method of benzenesulfonyl carboxamide compound provided by the invention (I) is as follows:
Concrete operations follow these steps to carry out:
With 1-[(6-chloro-3-pyridine) methyl]-2-imidazolone (II), organic amine, solvent such as methylene dichloride, trichloromethane, acetone, toluene, N, dinethylformamide is mixed, under agitation slowly adds various substituent benzene sulfonyl chloride, reacted 0.5-48 hour down at 40-150 ℃, reaction is cooled off with ice-water bath after finishing, with the anhydrous diethyl ether washing, use absolute ethanol washing again, filter, vacuum-drying promptly obtains compound (I) with anhydrous diethyl ether-ethyl alcohol recrystallization compound.
Reaction raw materials substituted benzene SULPHURYL CHLORIDE and 1-[(6-chloro-3-pyridine) methyl]-mol ratio of 2-imidazolone (II) is 1: 2-4: 1, and preferably than being 1.5: 1-3: 1.
Temperature of reaction is between 40-150 ℃, and preferred temperature is 60-120 ℃.
Reaction solvent is alkane, halogenated alkane, oxygenatedchemicals, nitrogenous compound, and generally speaking, solvent is little to the influence of reaction, still, carries out in order to make to be reflected under the suitable temperature, should consider the boiling point of reaction solvent.Preferred solvent comprises toluene, trichloromethane, acetonitrile and acetone etc.
Reaction times is 0.5-48 hour, and the preferred reaction times is 12-36 hour.
The consumption of organic amine and reactant substrate (I I) mol ratio 1: 2-4: 1, preferred mol ratio is 1: 1-1.5: 1.
The present invention has synthesized benzenesulfonyl carboxamide agricultural chemicals lead compound by one-step synthesis, and step is simple, and post-reaction treatment is convenient, and productive rate can reach more than 80%, has better industrial application prospect.
Embodiment
The following example can be used to further specify the present invention, but does not mean that restriction the present invention.
The preparation of compound (I)
Embodiment 1
In two mouthfuls of flasks of 250mL, add 1-[(6-chloro-3-pyridine) methyl]-2-imidazolone 5mmoL, acid binding agent triethylamine 5mmoL, methylene chloride 5mL, under mechanical stirring, slowly add benzene sulfonyl chloride 10mmoL, be warming up to reflux temperature then, refluxed 24 hours, after reaction finishes, with the ice-water bath cooling, (dehydrated alcohol (3 * 10mL) washings three times are used in 3 * 10mL) washings three times again with anhydrous diethyl ether, filter, vacuum-drying obtains compound 0.62g with anhydrous diethyl ether-ethyl alcohol recrystallization compound, productive rate 35%.Mp?165-167℃，
1H?NMR(CDCL
3，400MHz)δ：3.29(t，J＝8Hz，2H)，3.86(t，J＝8Hz，2H)，4.31(s，2H)，7.29(d，J＝8Hz，1H)，7.52-7.69(m，4H)，8.05(d，J＝8Hz，2H)，8.21(s，1H).
13C?NMR(100MHz，CDCL
3)δ：41.15，41.83，44.63，124.56，127.98，128.12，129.07，130.09，137.61，138.84，149.17，151.32，153.93.IR(KBr)：1723，1358，1176，1099，752cm
-1。
Embodiment 2
1-[(6-chloro-3-pyridine in two mouthfuls of flasks of 250mL) methyl]-2-imidazolone 5mmoL, acid binding agent triethylamine 5mmoL, solvent trichloromethane 5mL, under mechanical stirring, slowly add benzene sulfonyl chloride 10mmoL, be warming up to reflux temperature then, refluxed 24 hours, after reaction finishes, with the ice-water bath cooling, (dehydrated alcohol (10mL) washing three times are used in 3 * 10mL) washings three times again with anhydrous diethyl ether, filter, vacuum-drying obtains compound 1.23g with anhydrous diethyl ether-ethyl alcohol recrystallization compound, productive rate 70%.
Embodiment 3
1-[(6-chloro-3-pyridine in two mouthfuls of flasks of 250mL) methyl]-2-imidazolone 5mmoL, acid binding agent triethylamine 5mmoL, solvent acetone 5mL, under mechanical stirring, slowly add benzene sulfonyl chloride 10mmoL, be warming up to reflux temperature then, refluxed 24 hours, after reaction finishes, with the ice-water bath cooling, (dehydrated alcohol (10mL) washing three times are used in 3 * 10mL) washings three times again with anhydrous diethyl ether, filter, vacuum-drying obtains compound 1.26g with anhydrous diethyl ether-ethyl alcohol recrystallization compound, productive rate 72%.
Embodiment 4
1-[(6-chloro-3-pyridine in two mouthfuls of flasks of 250mL) methyl]-2-imidazolone 5mmoL, acid binding agent triethylamine 5mmoL, solvent acetonitrile 5mL, under mechanical stirring, slowly add benzene sulfonyl chloride 10mmoL, be warming up to reflux temperature then, refluxed 24 hours, after reaction finishes, with the ice-water bath cooling, (dehydrated alcohol (10mL) washing three times are used in 3 * 10mL) washings three times again with anhydrous diethyl ether, filter, vacuum-drying obtains compound 1.19g with anhydrous diethyl ether-ethyl alcohol recrystallization compound, productive rate 68%.
Embodiment 5
1-[(6-chloro-3-pyridine in two mouthfuls of flasks of 250mL) methyl]-2-imidazolone 5mmoL, acid binding agent triethylamine 5mmoL, solvent toluene 5mL, under mechanical stirring, slowly add benzene sulfonyl chloride 10mmoL, be warming up to reflux temperature then, refluxed 24 hours, after reaction finishes, with the ice-water bath cooling, (dehydrated alcohol (10mL) washing three times are used in 3 * 10mL) washings three times again with anhydrous diethyl ether, filter, vacuum-drying obtains compound 1.44g with anhydrous diethyl ether-ethyl alcohol recrystallization compound, productive rate 82%.
Embodiment 6
1-[(6-chloro-3-pyridine in two mouthfuls of flasks of 250mL) methyl]-2-imidazolone 5mmoL, acid binding agent triethylamine 5mmoL, solvent toluene 5mL, under mechanical stirring, slowly add fluorobenzene SULPHURYL CHLORIDE 10mmoL, be warming up to reflux temperature then, refluxed 24 hours, after reaction finishes, with the ice-water bath cooling, (dehydrated alcohol (10mL) washing three times are used in 3 * 10mL) washings three times again with anhydrous diethyl ether, filter, vacuum-drying obtains compound 1.55g with anhydrous diethyl ether-ethyl alcohol recrystallization compound, productive rate 84%.Mp145-146℃，
1H?NMR(CDCL
3，400MHz)δ：3.30(t，J＝8Hz，2H)，3.85(t，J＝8Hz，2H)，4.32(s，2H)，7.22-7.31(m，3H)，7.55(dd，J
1＝8Hz，J
2＝4Hz，1H)，8.07-8.11(m，2H)，8.22(d，J＝4Hz，1H).
13C?NMR(100MHz，CDCL
3)δ：41.24，41.81，44.74，116.42(J＝23Hz)，124.70，129.97，123.7(J＝9Hz)，138.89，149.23，151.32，153.93，162.08，165.96(J＝255Hz).IR(KBr)：1365，1356，1176，1719，1112，837，753cm
-1。
Embodiment 7
1-[(6-chloro-3-pyridine in two mouthfuls of flasks of 250mL) methyl]-2-imidazolone 5mmoL, acid binding agent triethylamine 5mmoL, solvent toluene 5mL, under mechanical stirring, slowly add p-bromobenzenesulfonyl chloride 10mmoL, be warming up to reflux temperature then, refluxed 24 hours, after reaction finishes, with the ice-water bath cooling, (dehydrated alcohol (10mL) washing three times are used in 3 * 10mL) washings three times again with anhydrous diethyl ether, filter, vacuum-drying obtains compound 1.78g with anhydrous diethyl ether-ethyl alcohol recrystallization compound, productive rate 83%.Mp125-126℃，
1H?NMR(CDCL
3，400MHz)δ：3.31(t，J＝8Hz，2H)，3.85(t，J＝8Hz，2H)，4.32(s，2H)，7.30(d，J＝8Hz，1H)，7.53(dd，J
1＝8Hz，J
2＝4Hz，1H)，7.70(d，J＝8Hz，2H)，7.92(d，J＝8Hz，2H)，8.22(d，J＝4Hz?1H).
13CNMR(100MHz，CDCL
3)δ：41.20，41.80，44.68，124.64，129.27，129.57，129.92，132.39，136.57，138.86，149.21，151.43，153.78.IR(KBr)：1716，1366，1169，1096，820，756，612，566cm
-1。
Embodiment 8
1-[(6-chloro-3-pyridine in two mouthfuls of flasks of 250mL) methyl]-2-imidazolone 5mmoL, acid binding agent triethylamine 5mmoL, solvent toluene 5mL, under mechanical stirring, slowly add parachloroben-zenesulfonyl chloride 10mmoL, be warming up to reflux temperature then, refluxed 24 hours, after reaction finishes, with the ice-water bath cooling, (dehydrated alcohol (10mL) washing three times are used in 3 * 10mL) washings three times again with anhydrous diethyl ether, filter, vacuum-drying obtains compound 1.66g with anhydrous diethyl ether-ethyl alcohol recrystallization compound, productive rate 86%.Mp162-164℃，
1H?NMR(CDCL
3，400MHz)δ：3.31(t，J＝8Hz，2H)，3.85(t，J＝8Hz，2H)，4.32(s，2H)，7.29(d，J＝8Hz，1H)，7.52-7.57(m，3H)，8.00(d，J＝8Hz，2H)，8.23(d，J＝4Hz?1H).
13C?NMR(100MHz，CDCL
3)δ：41.21，41.81，44.69，124.66，129.42，129.56，129.93，136.06，138.88，140.68，149.23，151.47，153.82.IR(KBr)：1735，1352，1170，823，765，753，619cm
-1。
Embodiment 9
1-[(6-chloro-3-pyridine in two mouthfuls of flasks of 250mL) methyl]-2-imidazolone 5mmoL, acid binding agent triethylamine 5mmoL, solvent toluene 5mL, under mechanical stirring, slowly add p-nitrophenyl SULPHURYL CHLORIDE 10mmoL, be warming up to reflux temperature then, refluxed 24 hours, after reaction finishes, with the ice-water bath cooling, (dehydrated alcohol (10mL) washing three times are used in 3 * 10mL) washings three times again with anhydrous diethyl ether, filter, vacuum-drying obtains compound 1.78g with anhydrous diethyl ether-ethyl alcohol recrystallization compound, productive rate 90%.Mp153-154℃，
1H?NMR(CDCL
3，400MHz)δ：3.34(t，J＝8Hz，2H)，3.91(t，J＝8Hz，2H)，4.33(s，2H)，7.31(d，J＝8Hz，1H)，7.55(dd，J
1＝8Hz，J
2＝4Hz，1H)，8.23(s，1H)，8.27(d，J＝8Hz，2H)，8.39(d，J＝8Hz，2H).
13C?NMR(100MHz，CDCL
3)δ：：41.32，41.85，44.78，124.27，124.72，129.56，129.71，138.92，143.17，149.24，150.82，151.59，153.46.IR(KBr)：1730，1538，1349，1177，1104，855，742，614cm
-1。
Embodiment 10
1-[(6-chloro-3-pyridine in two mouthfuls of flasks of 250mL) methyl]-2-imidazolone 5mmoL, acid binding agent triethylamine 5mmoL, solvent toluene 5mL, under mechanical stirring, slowly add p-methyl benzene sulfonic chloride 10mmoL, be warming up to reflux temperature then, refluxed 24 hours, after reaction finishes, with the ice-water bath cooling, (dehydrated alcohol (10mL) washing three times are used in 3 * 10mL) washings three times again with anhydrous diethyl ether, filter, vacuum-drying obtains compound 1.55g with anhydrous diethyl ether-ethyl alcohol recrystallization compound, productive rate 85%.Mp168-169℃，
1H?NMR(CDCL
3，400MHz)δ：2.45(s，3H)，3.27(t，J＝8Hz，2H)，3.84(t，J＝8Hz，2H)，4.31(s，2H)，7.28(d，J＝8Hz，1H)，7.35(d，J＝8Hz，2H)，7.53(dd，J
1＝8Hz，J
2＝4Hz，1H)，7.93(d，J＝8Hz，2H)，8.20(d，J＝4Hz?1H).
13C?NMR(100MHz，CDCL
3)δ：21.64，41.21，41.82，44.69，124.61，128.10，129.71，130.16，134.74，138.89，145.04，149.20，151.40，154.09.IR(KBr)：2926，1724，1357，1171，1095，810，755，742，671，578，547.
Embodiment 11
1-[(6-chloro-3-pyridine in two mouthfuls of flasks of 250mL) methyl]-2-imidazolone 5mmoL, acid binding agent triethylamine 5mmoL, solvent toluene 5mL, under mechanical stirring, slowly add ortho-nitrophenyl SULPHURYL CHLORIDE 10mmoL, be warming up to reflux temperature then, refluxed 24 hours, after reaction finishes, with the ice-water bath cooling, (dehydrated alcohol (10mL) washing three times are used in 3 * 10mL) washings three times again with anhydrous diethyl ether, filter, vacuum-drying obtains compound 1.78g with anhydrous diethyl ether-ethyl alcohol recrystallization compound, productive rate 90%.Mp157-158℃；
1H?NMR(CDCL
3，500MHz)δ：3.428(t，J＝7.5Hz，2H)，4.083(t，J＝7.5Hz，2H)，4.333(s，2H)，7.302(d，J＝8Hz，1H)，7.546(d，J＝8Hz，1H)，7.742-7.788(m，3H)，8.250(s，1H)，8.458(s，1H).
Embodiment 12
In two mouthfuls of flasks of 250mL, add 1-[(6-chloro-3-pyridine) methyl]-2-imidazolone 5mmoL, acid binding agent tripropylamine 5mmoL, solvent toluene 5mL, under mechanical stirring, slowly add benzene sulfonyl chloride 10mmoL, be warming up to reflux temperature then, refluxed 24 hours, after reaction finishes, with the ice-water bath cooling, (dehydrated alcohol (3 * 10mL) washings three times are used in 3 * 10mL) washings three times again with anhydrous diethyl ether, filter, vacuum-drying obtains compound 1.40g with anhydrous diethyl ether-ethyl alcohol recrystallization compound, productive rate 80%.
Embodiment 13
In two mouthfuls of flasks of 250mL, add 1-[(6-chloro-3-pyridine) methyl]-2-imidazolone 5mmoL, acid binding agent tributylamine 5mmoL, solvent toluene 5mL, under mechanical stirring, slowly add benzene sulfonyl chloride 10mmoL, be warming up to reflux temperature then, refluxed 24 hours, after reaction finishes, with the ice-water bath cooling, (dehydrated alcohol (3 * 10mL) washings three times are used in 3 * 10mL) washings three times again with anhydrous diethyl ether, filter, vacuum-drying obtains compound 1.36g with anhydrous diethyl ether-ethyl alcohol recrystallization compound, productive rate 77%.
Claims (5)
1, a kind of benzenesulfonyl carboxamide is characterized in that the structure of such benzenesulfonyl carboxamide is represented with general formula (I):
R is selected from hydrogen, halogen, C1-C10 alkyl, methoxyl group, nitro, trifluoromethyl or aldehyde radical in the general formula (I).
2, the preparation method of the described benzenesulfonyl carboxamide of a kind of claim 1, it is characterized in that this method is to add 1-[(6-chloro-3-pyridine in reaction vessel) methyl]-2-imidazolone, organic amine, solvent slowly add the benzene sulfonyl chloride of different substituents under mechanical stirring, reacted 0.5～48 hour down at 40～150 ℃, after reaction finishes, with the ice-water bath cooling,, filter with the anhydrous diethyl ether washing, vacuum-drying obtains described benzenesulfonyl carboxamide with anhydrous diethyl ether-ethyl alcohol recrystallization compound; Wherein: substituted benzene SULPHURYL CHLORIDE and 1-[(6-chloro-3-pyridine) methyl]-mol ratio of 2-imidazolone is 1: 2～4: 1; The consumption of organic amine and 1-[(6-chloro-3-pyridine) methyl]-mol ratio of 2-imidazolone is 1: 2～4: 1, solvent and 1-[(6-chloro-3-pyridine) methyl]-mol ratio of 2-imidazolone is 5: 1～25: 1.
3, method according to claim 2 is characterized in that described organic amine is catalyzer and acid binding agent; Organic amine is an alkylamine.
4, method according to claim 3 is characterized in that described alkylamine comprises triethylamine, tripropylamine and tributylamine.
5, method according to claim 2 is characterized in that described solvent is methylene dichloride, trichloromethane, acetone, toluene, acetonitrile or N, dinethylformamide.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102093338A (en) * | 2010-12-08 | 2011-06-15 | 华东师范大学 | N-acyl cyclic urea derivative and preparation method thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102093338A (en) * | 2010-12-08 | 2011-06-15 | 华东师范大学 | N-acyl cyclic urea derivative and preparation method thereof |
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Application publication date: 20091028 |