CN101597246B - Preparation method of 2-(3, 3, 3-trifluoro propyl) benzsulfamide (I) and midbody thereof - Google Patents

Preparation method of 2-(3, 3, 3-trifluoro propyl) benzsulfamide (I) and midbody thereof Download PDF

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CN101597246B
CN101597246B CN 200810110468 CN200810110468A CN101597246B CN 101597246 B CN101597246 B CN 101597246B CN 200810110468 CN200810110468 CN 200810110468 CN 200810110468 A CN200810110468 A CN 200810110468A CN 101597246 B CN101597246 B CN 101597246B
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propane
benzenesulfonamide
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CN101597246A (en
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孔繁蕾
陈书明
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江苏省农用激素工程技术研究中心有限公司
江苏省激素研究所有限公司
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Abstract

2-(3,3,3-三氟丙烷基)苯磺酰胺(I)的制备方法;4,5-二氯-2-(3,3,3-三氟丙烷基)苯磺酰胺(II)的氢化脱氯化反应;4,5-二氯-2-(3,3,3-三氟丙烷基)苯磺酰胺(II)由1,2-二氯-4-(3,3,3-三氟丙烷基)苯与氯磺酸,氨水或氨气反应得到。 2- (3,3,3-trifluoro-propane-yl) benzenesulfonamide (I); and 4,5-dichloro-2- (3,3,3-trifluoro-propane-yl) benzenesulfonamide (II ) hydrogenation dechlorination reaction; 4,5-dichloro-2- (3,3,3-trifluoro-propane-yl) benzenesulfonamide (II) from 1,2-dichloro-4- (3,3, propane-3-trifluoromethyl) benzene and chlorosulfonic acid, aqueous ammonia or ammonia reaction.

Description

2-(3,3, 3-三氟丙烷基)苯磺酰胺(I)及其中间体制备方 2- (3,3, 3- trifluoro-propane-yl) benzenesulfonamide (I) and intermediates preparing

law

技术领域 FIELD

[0001] 本发明属于2-(3,3,3-三氟丙烷基)苯磺酰胺(I)的一种制备方法;该化合物是 [0001] The present invention pertains to 2- (3,3,3-trifluoro-propane-yl) benzenesulfonamide A method for preparing formula (I); the compound is

制备一种生物活性物质的中间体。 Intermediate preparing a biologically active substance. 其结构式为: Its structural formula is:

[0002] [0002]

Figure CN101597246BD00031

背景技术 Background technique

[0003] 已知的2-(3,3,3-三氟丙烷基)苯磺酰胺⑴的制备方法步骤如下: [0003] Known 2- (3,3,3-trifluoro-propane-yl) benzenesulfonamide ⑴ preparation steps are as follows:

[0004] a)邻氨基苯磺酸与亚硝酸钠在酸性条件下重氮化反应与3,3,3-三氟_1_丙烯在均相催化剂pd(dba)2作用下反应,得到1-(3,3,3-三氟丙烯基)苯磺酸钠。 [0004] a) anthranilic acid with sodium nitrite under acidic conditions the diazotization reaction with 3,3,3-trifluoro _1_ propylene in homogeneous catalyst pd (dba) 2 under the action, to give 1 - (3,3,3-trifluoro-propenyl) benzene sulphonate.

[0005] b)得到的产品与5-10%钯碳在水或有机溶剂中加氢加压反应得到1-(3,3,3_三氟丙基)苯磺酸钠。 [0005] b) the product obtained with 5-10% palladium on carbon in water or an organic solvent, the hydrogenation reaction pressure to give 1- (3,3,3_ trifluoropropyl) benzenesulfonate.

[0006] c)l-(3,3,3_三氟丙烯基)苯磺酰胺与光气,二甲基甲酰胺和氨气进行酰胺化反应得至IJ 1-(3,3,3_三氟丙基)苯磺酰胺。 [0006] c) l- (3,3,3_ trifluoromethyl-propenyl) benzenesulfonamide amidation reaction with phosgene, dimethyl formamide and ammonia to give IJ 1- (3,3,3_ trifluoropropyl) benzenesulfonamide. (专利号EP120814,EP0584043 ;公开日1984年11月3日)。 (Patent No. EP120814, EP0584043; published on November 3, 1984).

[0007] 反应式如下: [0007] The reaction is as follows:

[0008] [0008]

Figure CN101597246BD00032

[0009] 一共4个阶段。 [0009] A total of four stages.

[0010] 本方法的缺点是使用价格昂贵的催化剂Pd(dba)2,原料3,3,3_三氟_1_丙烯为气体沸点-18°C,并且在酰胺化采用高毒性光气,合成成本较高和工业化操作比较困难。 [0010] The disadvantage of this method is the use of expensive catalyst Pd (dba) 2, raw material propylene gas 3,3,3_ trifluoromethyl _1_ boiling point -18 ° C, and an amidation using highly toxic phosgene, the higher cost of synthesis and industrial operations more difficult.

发明内容 SUMMARY

[0011] 本发明完全采用新的路线合成2-(3,3,3-三氟丙烷基)苯磺酰胺(I);本发明的路线完全可以排除以上缺点,而采用经济可行及操作简便的方法生产,成本较低,工业化操作很简单。 [0011] The present invention is completely new route Synthesis of 2- (3,3,3-trifluoro-propane-yl) benzenesulfonamide (the I); the route of the present invention can exclude the above drawbacks, the use of a simple and economically feasible method of production, low cost, industrial operation is very simple.

[0012] 本发明内容:一是4,5-二氯_2-(3,3,3-三氟丙烷基)苯磺酰胺(II)的制备。 SUMMARY [0012] The present invention: Preparation of 4,5-dichloro-one _2- (3,3,3-trifluoro-propane-yl) benzenesulfonamide (II) is. 通过1,2- 二氯-4-(3,3,3-三氟丙烷基)苯与氯磺酸反应,得到的产品用氨水或氨气在有机溶剂与水相中反应,反应完毕,用已知方法分离得到。 By 1,2-dichloro-4- (3,3,3-trifluoro-propane-yl) benzene sulfonic acid is reacted with chlorine, the product obtained with ammonia or ammonia in an organic solvent phase with water, the reaction is completed, with known methods isolated. 二是2-(3,3,3-三氟丙烷基)苯磺酰胺(I)的制备。 Second Preparation of 2- (3,3,3-trifluoro-propane-yl) benzenesulfonamide (I),. 通过4, 5-二氯-2-(3, 3, 3-二氟丙烧基)苯磺酰胺(II)与碱土金属氢氧化物溶液;5_10%钯碳催化剂在有机溶剂中氢化反应,然后用已知方法分离出产品。 By 4, 5-dichloro-2- (3, 3, 3-fluoro-propan-burn-yl) benzenesulfonamide (II) with an alkaline earth metal hydroxide solution; 5_10% palladium on carbon catalyst for the hydrogenation reaction in an organic solvent, and then the product was isolated by known methods.

[0013] 反应式如下: [0013] The reaction is as follows:

[0014] [0014]

Figure CN101597246BD00041

[0015] 本发明采用的常规的化学反应单元进行的,分2个阶段;第一阶段:是采用苯环磺化法生成磺酰氯,然后用氨水或氨气进行氨解中和。 [0015] to a conventional chemical reaction unit employed in the present invention, in two stages; first stage: a benzene ring is sulfonated using a sulfonyl chloride generating method, and then subjected to aminolysis with ammonia or ammonia. 反应平稳好操作。 Good smooth response operations. 第二阶段:采用的催化脱氯法,在碱液、催化剂存在的条件下,通氢气在常压到IOOatm范围内进行反应,反应条件温和,安全。 The second stage: catalytic dechlorination method is employed, under alkaline conditions in the presence of a catalyst, hydrogen gas at atmospheric pressure to pass the IOOatm range of the reaction, the reaction conditions are mild and safe.

[0016] 总之本发明的技术方案是: [0016] In summary aspect of the present invention is:

[0017] 2-(3,3,3-三氟丙烷基)苯磺酰胺⑴的合成方法 [0017] 2- (3,3,3-trifluoro-propane-yl) benzenesulfonamide The method of ⑴

[0018] [0018]

^^so2m2 ^^ so2m2

(I ) (I)

[0019] 包括以下阶段: [0019] includes the following phases:

[0020] &)1,2-二氯-4-(3,3,3_三氟丙烷基)苯与氯磺酸在有机溶剂或两者直接反应,得到的产品用氨水或氨气在有机溶剂与水相中反应,反应完毕,用已知方法分离得到4,5-二氯-2-(3, 3, 3-二氟丙烧基)苯磺酰胺(II)。 [0020] &) of 1,2-dichloro-4- (trifluoromethyl 3,3,3_ propane-yl) benzene directly with chlorosulfonic acid in an organic solvent, or both, the resulting product with aqueous ammonia or ammonia gas in an organic the reaction solvent in the aqueous phase, completion of the reaction, to give 4,5-dichloro-known separation methods using 2- (3, 3, 3-fluoro-propan-burn-yl) benzenesulfonamide (II).

[0021] [0021]

Figure CN101597246BD00051

(II) (II)

[0022] b) 4,5-二氯-2-(3,3,3-三氟丙烷基)苯磺酰胺(II)与碱土金属氢氧化物溶液;钯碳催化剂在有机溶剂中反应,然后用已知方法分离出产品2-(3,3,3_三氟丙烷基)苯磺酰胺⑴。 [0022] b) 4,5- dichloro-2- (3,3,3-trifluoro-propane-yl) benzenesulfonamide (II) with an alkaline earth metal hydroxide solution; palladium on carbon catalyst in an organic solvent, and then the product was isolated 2- (trifluoromethyl 3,3,3_ propane-yl) benzenesulfonamide ⑴ by known methods.

[0023] 2-(3,3,3_三氟丙烷基)苯磺酰胺(I)合成方法,其特征在于碱土金属氢氧化物溶液,钯碳催化剂(氢化脱氯)与由1,2_ 二氯-4-(3,3,3-三氟丙烷基)苯,氯磺酸,氨水或氨气反应得到的物料反应;然后用已知方法分离得到产品2-(3,3,3-三氟丙烷基)苯磺酰胺⑴。 [0023] 2- (trifluoromethyl 3,3,3_ propane-yl) benzenesulfonamide (I) synthesis process, which is characterized in that the alkaline earth metal hydroxide solution, palladium on carbon catalyst (hydrogenation dechlorination) by the two 1,2_ chloro-4- (3,3,3-trifluoro-propane-yl) benzene, chlorosulfonic acid, aqueous ammonia or ammonia gas obtained by reacting a reaction mass; the product obtained is then isolated by known methods 2- (3,3,3- heptafluoropropane yl) benzenesulfonamide ⑴.

[0024] 2-(3,3,3-三氟丙烷基)苯磺酰胺(I)合成方法,其特征在于反应时加入的催化剂为钯碳催化剂。 [0024] 2- (3,3,3-trifluoro-propane-yl) benzenesulfonamide (I) synthesis process, wherein the catalyst added during the reaction is palladium on carbon.

[0025] 2-(3,3,3-三氟丙烷基)苯磺酰胺(I)合成方法,其特征在于反应时加入的碱土金属氢氧化物溶液为氢氧化钠,氢氧化钾中的任一种,浓度0-30%。 (3,3,3-trifluoro-propane-yl) benzenesulfonamide (I) synthesis process, which is characterized in that any of sodium hydroxide was added during the reaction of an alkaline earth metal hydroxide solution [0025] 2- one of a concentration of 0-30%.

[0026] 一种生产2-(3,3,3_三氟丙烷基)苯磺酰胺(I)的中间体4,5_ 二氯_2_(3,3,3_三氟丙烷基)苯磺酰胺(II)的合成方法,其特征在于 [0026] A method of producing 2- (trifluoromethyl 3,3,3_ propane-yl) benzenesulfonamide (I), intermediates 4,5_ dichloro _2_ (trifluoromethyl 3,3,3_ propane-yl) benzenesulfonamide amide (II) is synthesized, characterized in that

[0027] I,2-二氯-4-(3,3,3-三氟丙烷基)苯与氯磺酸在有机溶剂或两者直接反应,得到的产品用氨水或氨气在有机溶剂与水相中反应,反应完毕,用已知方法分离得到4,5-二氯-2-(3, 3, 3-二氟丙烧基)苯磺酰胺(II)。 [0027] I, 2- dichloro-4- (3,3,3-trifluoro-propane-yl) benzene directly with chlorosulfonic acid in an organic solvent, or both, the resulting product with aqueous ammonia or ammonia gas in an organic solvent The reaction aqueous phase, completion of the reaction, to give 4,5-dichloro-known separation methods using 2- (3, 3, 3-fluoro-propan-burn-yl) benzenesulfonamide (II).

[0028] 下面结合实施例对本发明进行进一步地详细说明。 [0028] The present invention will be described in further detail in conjunction with embodiments.

具体实施方式 Detailed ways

[0029] 下面将描述本发明的几个实施例,进一步说明本发明,但本发明的内容完全不局限与此 Several [0029] The present invention will be described in the following embodiments, the present invention is further illustrated, but the present invention is not limited thereto completely

[0030] 实施例1 4,5-二氯-2-(3,3,3-三氟丙烷基)苯磺酰胺(II)的合成方法。 1 4,5-dichloro-2- (3,3,3-trifluoro-propane-yl) benzenesulfonamide (II) synthesis method [0030] Example.

[0031 ] 在烧瓶中加入5.7ml氯磺酸,冰盐冷却至O °C ;滴加5.0g (0.029mol) I,2_ 二氯-4- (3,3,3-三氟丙烷基)苯,控温在小于50°C,约I小时加完;在0-5°C反应4小时,反应液变成黄棕色粘稠油状物;将20g冰和5ml冰水,置于冰浴中;将反应液缓慢倒入冰水中,边搅拌边控温小于10-15°C ;析出白色固体,冷却15min,抽滤得产品(MS:340);加入IOml二氯乙烷,搅拌溶解后冷却至0°C,滴加过量氨水,反应液升温小于40°C ;滴毕,至室温,pH=8-9 ;抽滤,水洗得到白色固体产品4,5-二氯-2-(3,3,3-三氟丙烷基)苯磺酰胺(II)(MS:321);收率为81%。 [0031] 5.7ml of chlorosulfonic acid was added in the flask, ice-salt cooled to O ° C; solution of 5.0g (0.029mol) I, 2_-dichloro-4- (3,3,3-trifluoro-propane-yl) benzene , at temperature less than 50 ° C, for about I hour addition was completed; reaction 0-5 ° C 4 hours, the reaction liquid became a yellow-brown viscous oil; 20g of ice and 5ml of ice water, placed in an ice bath; the reaction mixture was slowly poured into ice water with stirring temperature less than 10-15 ° C; white solid precipitated, cooled 15min, filtered off with suction to give the product (MS: 340); after IOml dichloroethane was added, and dissolved with stirring to a cooled 0 ° C, excess ammonia was added dropwise, the reaction was warmed less than 40 ° C; dropwise, to room temperature, pH = 8-9; filtered off with suction, washed with water to give a white solid product 4,5-dichloro-2- (3,3 , propane-3-trifluoromethyl-yl) benzenesulfonamide (II) (MS: 321); 81% yield. 产品经液相色谱分析含量为93.4%。 Product analyzed by HPLC content of 93.4%.

[0032] 实施例2 4,5-二氯-2-(3,3,3-三氟丙烷基)苯磺酰胺(II)的合成方法。 2 4,5-dichloro-2- (3,3,3-trifluoro-propane-yl) benzenesulfonamide (II) synthesis method [0032] Example. [0033] 在烧瓶中加入5.7ml氯磺酸,冰盐冷却至O °C ;滴加5.0g (0.029mol) I,2_ 二氯-4-(3,3,3-三氟丙烷基)苯,控温在小于10°C,约I小时加完;升温至室温,反应液变成黄棕色粘稠油状物;搅拌反应5小时,将20g冰和5ml冰水,置于冰浴中;将反应液缓慢倒入冰水中,边搅拌边控温小于10-15°C ;析出白色固体,冷却15min,抽滤得产品(MS:340);力口入IOml 二氯乙烷,搅拌溶解后冷却至0°C,滴加过量氨水,反应液升温小于40°C;滴毕,至室温,pH = 8-9 ;抽滤,水洗得到白色固体产品4,5- 二氯-2-(3,3,3-三氟丙烷基)苯磺酰胺 [0033] 5.7ml of chlorosulfonic acid was added in the flask, ice-salt cooled to O ° C; solution of 5.0g (0.029mol) I, 2_-dichloro-4- (3,3,3-trifluoro-propane-yl) benzene , at temperature less than 10 ° C, for about I hour addition was completed; warmed to room temperature, the reaction solution became a yellow-brown viscous oil; reaction was stirred for 5 hours, 5ml of ice water and 20g of ice, placed in an ice bath; and the reaction solution was slowly poured into ice water with stirring temperature less than 10-15 ° C; white solid precipitated, cooled 15min, filtered off with suction to give the product (MS: 340); after the force mouth IOml dichloroethane, cooled with stirring to dissolve to 0 ° C, excess ammonia was added dropwise, the reaction was warmed less than 40 ° C; dropwise, to room temperature, pH = 8-9; filtered off with suction, washed with water to give a white solid product 4,5-dichloro-2- (3, 3,3,3-trifluoro-propane-yl) benzenesulfonamide

(II) (MS:321);收率为83%。 (II) (MS: 321); 83% yield. 产品经液相色谱分析含量为94.5%。 Product analyzed by HPLC content 94.5%.

[0034] 实施例3 4,5-二氯-2-(3,3,3-三氟丙烷基)苯磺酰胺(II)的合成方法。 3 4,5-dichloro-2- (3,3,3-trifluoro-propane-yl) benzenesulfonamide (II) synthesis method [0034] Example.

[0035] 在烧瓶中加入5.7ml氯磺酸,冰盐冷却至O °C ;滴加5.0g (0.029mol) I,2_ 二氯-4-(3,3,3-三氟丙烷基)苯,控温在小于10°C,约I小时加完;升温至室温,水浴加热55°C为4小时,反应液变成黄棕色粘稠油状物;将20g冰和5ml冰水,置于冰浴中;将反应液缓慢倒入冰水中,边搅拌边控温小于10_15°C;析出白色固体,冷却15min,抽滤得产品(MS:340);加入IOml 二氯乙烷,搅拌溶解后冷却至0°C,通过量氨气,反应液升温小于40°C ;滴毕,至室温,pH = 8-9 ;浓缩、水洗、过滤得到白色固体产品4,5-二氯-2-(3,3,3-三氟丙烷基)苯磺酰胺(II) (MS:321);收率为87%。 [0035] 5.7ml of chlorosulfonic acid was added in the flask, ice-salt cooled to O ° C; solution of 5.0g (0.029mol) I, 2_-dichloro-4- (3,3,3-trifluoro-propane-yl) benzene , at temperature less than 10 ° C, for about I hour addition was completed; warmed to room temperature, 55 ° C water bath for 4 hours, the reaction liquid became a yellow-brown viscous oil; 20g of ice and 5ml of ice water, placed in an ice bath; the reaction was slowly poured into ice water with stirring temperature of less than 10_15 ° C; white solid precipitated, cooled 15min, filtered off with suction to give the product (MS: 340); after IOml dichloroethane was added, and dissolved with stirring cooling to 0 ° C, by the amount of ammonia, the reaction was warmed less than 40 ° C; dropwise, to room temperature, pH = 8-9; concentrated, washed with water and filtered to give a white solid product 4,5-dichloro-2- (3 , 3,3,3-trifluoro-propane-yl) benzenesulfonamide (II) (MS: 321); 87% yield. 产品经液相色谱分析含量为98%。 Product analyzed by HPLC contained about 98%.

[0036] 实施例4 2-(3,3,3-三氟丙烷基)苯磺酰胺⑴的合成方法。 42- benzenesulfonamide ⑴ synthesis of (3,3,3-trifluoro-propane-yl) Example [0036] FIG.

[0037] 在烧瓶中加入5g 4,5-二氯_2-(3,3,3-三氟丙烷基)苯磺酰胺(II),再分别加入100ml5%氢氧化钠溶液,50ml叔丁醇,0.2gPd_°C;排空气,在钯碳催化剂下通氢气。 [0037] Add 5g 4,5- dichloro flask _2- (3,3,3-trifluoro-propane-yl) benzenesulfonamide (II), and then were added 100 ml of 5% sodium hydroxide solution, 50ml tert-butanol , 0.2gPd_ ° C; air venting, through hydrogen under palladium on carbon catalyst. 并升温50-60°C ;常温反应约需20小时,TLC中控;反应完毕,浓缩后,加IOml水,冷却用2N盐酸调pHl-2,析出白色固体2-(3,3,3-三氟丙烷基)苯磺酰胺(I) (HPLC-MS:253),过滤,烘干。 And heated 50-60 ° C; the reaction at room temperature about 20 hours, TLC in the control; completion of the reaction, was concentrated, water was added IOml, adjusted with 2N hydrochloric acid, cooled pHl-2, precipitation of a white solid of 2- (3,3,3- trifluoro-propane-yl) benzenesulfonamide (I) (HPLC-MS: 253), filtering and drying. 收率95%,产品经液相色谱分析含量为88%。 95% yield, the product was analyzed by liquid chromatography content of 88%.

[0038] 实施例5 2-(3,3,3-三氟丙烷基)苯磺酰胺(I)的合成方法 52- (3,3,3-trifluoro-propane-yl) benzenesulfonamide (I) Example of synthesis of [0038] Embodiment

[0039] 在压力釜中加入5g 4,5_ 二氯-2_(3,3,3-三氟丙烷基)苯磺酰胺(II),再分别加入100ml5%氢氧化钠溶液,50ml水,0.2gPd_C ;排空气,在IE碳催化剂下通氢气。 [0039] Add 5g 4,5_ autoclave -2_ dichloro (3,3,3-trifluoro-propane-yl) benzenesulfonamide (II), and then were added 100 ml of 5% sodium hydroxide solution, 50ml water, 0.2gPd_C ; exhaust air, through IE carbon catalyst under hydrogen. 3atm压力下常温反应约需16小时,反应完毕,浓缩后,加IOml水,冷却用2N盐酸调ρΗ1_2,析出白色固体2-(3,3,3_三氟丙烷基)苯磺酰胺(I) (HPLC-MS:253),过滤,烘干。 3atm pressure at room temperature the reaction takes about 16 hours, completion of the reaction, was concentrated, water was added IOml cooled with 2N hydrochloric ρΗ1_2, precipitated as a white solid 2- (trifluoromethyl 3,3,3_ propane-yl) benzenesulfonamide (I) (HPLC-MS: 253), filtering and drying. 收率96%,产品经液相色谱分析含量为91 %。 Yield 96%, content of the product by HPLC analysis was 91%.

[0040] 实施例6 2- (3,3,3-三氟丙烷基)苯磺酰胺⑴的合成方法 62- benzenesulfonamide ⑴ synthesis of (3,3,3-trifluoro-propane-yl) Example [0040] Embodiment

[0041] 在压力釜中加入5g 4,5_ 二氯-2_(3,3,3-三氟丙烷基)苯磺酰胺(II),再分别加入100ml5%氢氧化钠溶液,50ml丙酮,0.2gPd_C ;排空气,在IE碳催化剂下通氢气。 [0041] Add 5g 4,5_ autoclave -2_ dichloro (3,3,3-trifluoro-propane-yl) benzenesulfonamide (II), and then were added 100 ml of 5% sodium hydroxide solution, 50ml of acetone, 0.2gPd_C ; exhaust air, through IE carbon catalyst under hydrogen. IOatm压力下常温反应约需12小时,反应完毕,浓缩后,加IOml水,冷却用2N盐酸调ρΗ1_2,析出白色固体2-(3,3,3-三氟丙烷基)苯磺酰胺(I) (HPLC-MS:253),过滤,烘干。 At room temperature, the reaction pressure IOatm Approximately 12 hours completion of the reaction, was concentrated, water was added IOml cooled with 2N hydrochloric ρΗ1_2, precipitated as a white solid of 2- (3,3,3-trifluoro-propane-yl) benzenesulfonamide (I) (HPLC-MS: 253), filtering and drying. 收率94%,产品经液相色谱分析含量为90%。 Yield 94%, content of the product by liquid chromatography was 90%.

Claims (2)

1.2- (3,3,3-三氟丙烷基)苯磺酰胺(I)的合成方法, 1.2 (3,3,3-trifluoro-propane-yl) benzenesulfonamide (I), and
Figure CN101597246BC00021
包括以下阶段: a) I,2-二氯-4- (3,3,3-三氟丙烷基)苯与氯磺酸在有机溶剂或两者直接反应,得到的产品用氨水或氨气在有机溶剂与水相中反应,反应完毕,用已知方法分离得到4,5- 二氯-2- (3,3,3-二氟丙烧基)苯磺酰胺(II ); It comprises the following stages: a) I, 2- dichloro-4- (3,3,3-trifluoro-propane-yl) benzene direct reaction with chlorosulfonic acid in an organic solvent or both, in the obtained product with ammonia or ammonia organic solvent in the aqueous phase of the reaction, the reaction is complete, isolated by known methods to obtain 4,5-dichloro-2- (3,3-difluoro-prop-burn-yl) benzenesulfonamide (II);
Figure CN101597246BC00022
b) 4,5-二氯-2- (3,3,3-三氟丙烷基)苯磺酰胺(II )与碱土金属氢氧化物溶液;.5-10%钯碳催化剂在有机溶剂中反应,然后用已知方法分离出产品2-(3,3,3_三氟丙烷基)苯磺酰胺(I)。 b) 4,5- dichloro-2- (3,3,3-trifluoro-propane-yl) benzenesulfonamide (II) with an alkaline earth metal hydroxide solution; .5-10% palladium on carbon catalyst in an organic solvent and isolating the product 2- (trifluoromethyl 3,3,3_ propane-yl) benzenesulfonamide (I) by known methods.
2.根据权利要求1的2- (3,3,3_三氟丙烷基)苯磺酰胺(I )合成方法,其特征在于反应时加入的催化剂为5-10%钯碳催化剂。 The 2- (trifluoromethyl 3,3,3_ propane-yl) benzenesulfonamide (I) as claimed in claim 1 synthesis method, wherein a reaction catalyst is added at the 5-10% palladium on carbon catalyst.
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0120814A2 (en) 1983-03-28 1984-10-03 Ciba-Geigy Ag N-phenylsulfonyl-N'-pyrimidinyl- and -triazinyl urea
CN1083480A (en) 1992-08-18 1994-03-09 希巴-盖吉股份公司 Process for the preparation of substituted benzenes and benzene sulfonic acid and derivatives thereof and a process for the preparation of N,N'-substituted ureas

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0120814A2 (en) 1983-03-28 1984-10-03 Ciba-Geigy Ag N-phenylsulfonyl-N'-pyrimidinyl- and -triazinyl urea
CN1083480A (en) 1992-08-18 1994-03-09 希巴-盖吉股份公司 Process for the preparation of substituted benzenes and benzene sulfonic acid and derivatives thereof and a process for the preparation of N,N'-substituted ureas

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHRISTOPHE MENNITI et al.Soil Transformation of Prosulfuron.《J. Agric. Food Chem.》.2003,第51卷(第12期),3525-3527.

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