JPH045667B2 - - Google Patents
Info
- Publication number
- JPH045667B2 JPH045667B2 JP8985084A JP8985084A JPH045667B2 JP H045667 B2 JPH045667 B2 JP H045667B2 JP 8985084 A JP8985084 A JP 8985084A JP 8985084 A JP8985084 A JP 8985084A JP H045667 B2 JPH045667 B2 JP H045667B2
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- phosphorus oxychloride
- reaction
- nitrobenzenesulfonamide
- organic medium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 26
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- COZWQPZDKVIVFS-UHFFFAOYSA-N 2-chloro-5-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(S(Cl)(=O)=O)=C1 COZWQPZDKVIVFS-UHFFFAOYSA-N 0.000 claims description 6
- OUERFXCJVYJQJO-UHFFFAOYSA-M sodium;2-chloro-5-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=C(Cl)C(S([O-])(=O)=O)=C1 OUERFXCJVYJQJO-UHFFFAOYSA-M 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- GNDKYAWHEKZHPJ-UHFFFAOYSA-N 2-nitrobenzenesulfonimidic acid Chemical compound NS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O GNDKYAWHEKZHPJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 2
- ZAJALNCZCSSGJC-UHFFFAOYSA-N 2-chloro-5-nitrobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1Cl ZAJALNCZCSSGJC-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- 235000011114 ammonium hydroxide Nutrition 0.000 description 6
- 239000005457 ice water Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- GNTARUIZNIWBCN-UHFFFAOYSA-N 2-chloro-5-nitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1Cl GNTARUIZNIWBCN-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- HQSLKNLISLWZQH-UHFFFAOYSA-N 1-(2-propoxyethoxy)propane Chemical compound CCCOCCOCCC HQSLKNLISLWZQH-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- SDHXWAPVLOGAJR-UHFFFAOYSA-N 2-chloro-5-nitrobenzamide Chemical compound NC(=O)C1=CC([N+]([O-])=O)=CC=C1Cl SDHXWAPVLOGAJR-UHFFFAOYSA-N 0.000 description 1
- WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- -1 glycol ethers Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000273 veterinary drug Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は２−クロル−５−ニトロベンゼンスル
ホンアミドの製造方法、さらに詳しくは２−クロ
ル−５−ニトロベンゼンスルホン酸ナトリウム
を、過剰のオキシ塩化リンで２−クロル−５−ニ
トロベンゼンスルホン酸クロライドとし、次に有
機媒体として、沸点範囲120〜300℃を有するグリ
コールエーテル又は脂肪族、脂環式あるいは芳香
族の炭化水素を加えた後、過剰のオキシ塩化リン
を留去、置換し、続いて、アンモニア水で反応す
ることを特徴とする２−クロル−５−ニトロベン
ゼンスルホンアミドの製造方法に関するものであ
る。
２−クロル−５−ニトロベンゼンアミドは動物
用医薬品の原体として近年になつて需要を伸ばし
つつある化学物質である。
従来、２−クロル−５−ニトロベンゼンスルホ
ンアミドの製造法では、２−クロル−５−ニトロ
ベンゼンスルホン酸を原料とし、クロルスルホン
酸を使用して２−クロル−５−ニトロベンゼンス
ルホン酸クロライドを得、次いでアンモニア水を
加えて合成されることが知られている（特開昭53
−65884公報）。しかし、この方法（前半）（第１
段反応）は反応終了後、氷水に注ぎ入れる必要が
あり、工業規模では大きな危険を伴ない、又、収
率も低いので、実用上工業的方法とは言い難い。
また、ベンゼンスルホン酸あるいはベンゼンス
ルホン酸ナトリウムを原料とし、オキシ塩化リ
ン、三塩化リン、五塩化リン及びチオニルククロ
ライド等のクロル化剤を使用して２−クロル−５
−ニトロベンゼンスルホン酸クロライドを得るこ
とも知られている。（実験化学講座20巻80頁＝丸
善）しかし、この場合も反応終了後、氷水に注ぎ
入れる方式で工業的な方法とは言い難い。
本発明者等は鋭意検討を重ねた結果、２−クロ
ル−５−ニトロベンゼンスルホンアミドの新規な
工業的製造法を見い出したものである。
即ち、本発明の方法は安価に入手可能な２−ク
ロル−５−ニトロベンゼンスルホン酸ナトリウム
を出発原料とし、これを過剰のオキシ塩化リンで
クロル化して、２−クロル−５−ニトロベンゼン
スルホン酸クロライドのスラリーを得る（第１段
反応）。次に、過剰のオキシ塩化リンを回収する
に際し、置換溶媒として特定の有機媒体を加えた
後に、オキシ塩化リンを留去する。続いて、ここ
で得られた２−クロル−５−ニトロベンゼンスル
ホン酸クロライドのスラリーをアンモニア水でア
ミド化して、２−クロル−５−ニトロベンゼンス
ルホンアミドを合成する（第２段反応）方法であ
る。
本発明の特徴は特定の有機媒体の使用及びその
使用場所によつて一貫した適度なスラリー状態で
の反応及び円滑な２工程の結合を導き出した工業
的に極めて優れたプロセスにある。
具体的には、第１段反応後、オキシ塩化リン
（第１段反応での溶媒でもある）の置換溶媒とし
て特定の有機媒体を用いることで、オキシ塩化リ
ンを留去した後に、２−クロル−５−ニトロベン
ゼンスルホン酸クロライドが固化するのを防いで
いること。さらに、第２段反応後、これを遠心分
離で別した液から分相するだけで容易に回
収、リサイクル出来ることである。
本発明における反応式は次の如く想定される。
本発明に適用される有機媒体としては、沸点範
囲120〜300℃を有するグリコールエーテル又は脂
肪族、脂環式あるいは芳香族炭化水素が挙げら
れ、具体的にはエチレングリコールジエチルエー
テル、エチレングリコールジプロピルエーテル；
石油留分、ドデカン、テトラデカン；デカヒドロ
ナフタリン、ジシクロヘキシル；キシレン、クメ
ン等が例示される。さらに上記範ちゆうに入いる
同ハロゲン化物、例えば、テトラクロルエタン等
も使用できる。この中、経済的には沸点約200℃
を有する炭化水素系石油留分、例えば潤滑油（市
販品）が好ましい。
有機媒体の使用量は対象液のスラリー濃度が適
度（約30％）となるように選ばれるが、原料２−
クロル−５−ニトロベンゼンスルホン酸ナトリウ
ムに対して２〜４重量倍が適当である。なお、第
１段反応に直接この有機媒体を使用するとき、該
反応は全く進行せず不可である。
本発明における各反応は固体を中心とした固液
反応であり、工業化技術上は煩雑で、且つ面倒な
問題を伴うが、通常次の操作条件が採用される。
第１段反応ではオキシ塩化リンの使用量は原料
２−クロル−５−ニトロベンゼンスルホン酸ナト
リウムに対して５〜10モル倍（過剰）が適当であ
る。温度は還流温度（約110℃）で実施される。
第２段反応では稀釈水の使用量は対象液に対し
て同一容量倍が適当であり、ここで残存していた
オキシ塩化リンが完全に消滅される。さらにアン
モニア水の使用量は中間体、２−クロル−５−ニ
トロベンゼンスルホン酸クロライドに対して５〜
10モル倍（過剰）が適当である。温度は還流温度
（約110℃）で実施される。
かくして得られた目的物２−クロル−５−ニト
ロベンゼンスルホンアミドを含む粗液は常法に従
つて過水洗及び乾燥を経て製品化される。なお
必要に応じて、活性炭処理、メタノール再結晶等
によつて一層高品位の製品とすることができる。
以下、本発明を実施例及び比較例によつてさら
に具体的に説明するが、これによつて本発明は何
ら限定されるものではない。
実施例 １
撹拌機付500mlフラスコを使用して、２−クロ
ル−５−ニトロベンゼンスルホン酸ナトリウム50
ｇ（0.193モル）及びオキシ塩化リン200ｇ（1.32
モル）を投入して油浴上で還流下（約110℃）20
時間加熱した。
反応後、有機媒体として炭化水素系石油留分
（沸点200〜260℃）（Ａ社製潤滑油）100ｇを加え、
再加熱して過剰のオキシ塩化リンを留去（回収）
した。
続いて、水300ｇで稀釈した後、23％アンモニ
ア水80ｇ（1.08モル）を加えて油浴上で還流下
（約110℃）30分間加熱した。
次に、冷却後常法に従つて過、水洗し、さら
に100℃×８時間、減圧乾燥させて、淡黄色結晶
37ｇ（0.156モル）を得た。（収率80.8％）この結
晶は質量分析及びＨ−NMRから２−クロル−５
−ニトロベンゼンスルホンアミドであることを確
認した。
比較例 １
特開昭58−65884公報記載の方法（有機媒体ナ
シ）に従つて、２−クロル−５−ニトロベンゼン
スルホン酸10ｇ（0.042モル）に、クロルスルホ
ン酸50ｇ（0.429モル）を加えて、５時間反応さ
せた。後、氷水500ｇに注入して２−クロル−５
−ニトロベンゼンクロライドを得た。
続いて、別した滓に28％アンモニア水10ｇ
（0.165モル）を加え、１時間反応させた。後、
別し乾燥して、２−クロル−５−ニトロベンゼン
スルホンアミド4.4ｇ（0.019モル）を得た。（収
率44.3％）
この方法によると危険物取扱い上、禁水物質で
あるクロルスルホン酸を氷水に注入する操作があ
り、実験室的にも工業的にも極めて危険である。
しかも収率は非常に低い。
比較例 ２
実施例１において、炭化水素系石油留分を第１
段反応開始前から加えて、同様の操作を行なつた
が、目的とする２−クロル−５−ニトロベンゼン
スルホンアミドは得られなかつた。
実施例 ２〜４
実施例１において有機媒体として表１に示した
化合物200ｇを使用した以外、同様な操作を行な
い、次の結果（表１）を得た。
【表】DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing 2-chloro-5-nitrobenzenesulfonamide, and more particularly, to a process for producing 2-chloro-5-nitrobenzenesulfonamide, in which sodium 2-chloro-5-nitrobenzenesulfonate is treated with excess phosphorus oxychloride. After adding nitrobenzenesulfonic acid chloride and then adding glycol ether or aliphatic, alicyclic or aromatic hydrocarbon having a boiling point range of 120 to 300°C as an organic medium, excess phosphorus oxychloride is distilled off and replaced. The present invention relates to a method for producing 2-chloro-5-nitrobenzenesulfonamide, which is characterized in that the present invention is then reacted with aqueous ammonia. 2-Chlor-5-nitrobenzenamide is a chemical substance whose demand has been increasing in recent years as a raw material for veterinary drugs. Conventionally, in the production method of 2-chloro-5-nitrobenzenesulfonamide, 2-chloro-5-nitrobenzenesulfonic acid is used as a raw material, chlorosulfonic acid is used to obtain 2-chloro-5-nitrobenzenesulfonic acid chloride, and then 2-chloro-5-nitrobenzenesulfonic acid chloride is obtained. It is known that it can be synthesized by adding aqueous ammonia (Japanese Unexamined Patent Publication No. 53
-65884). However, this method (first half) (first half)
Step reaction) requires pouring into ice water after the reaction is completed, which is very dangerous on an industrial scale, and the yield is low, so it cannot be called a practical industrial method. In addition, 2-chloro-5
It is also known to obtain -nitrobenzenesulfonic acid chloride. (Jikken Chemistry Course Vol. 20, p. 80 = Maruzen) However, in this case as well, the mixture is poured into ice water after the reaction is complete, so it can hardly be called an industrial method. As a result of extensive research, the present inventors have discovered a new industrial method for producing 2-chloro-5-nitrobenzenesulfonamide. That is, the method of the present invention uses inexpensively available sodium 2-chloro-5-nitrobenzenesulfonate as a starting material, which is chlorinated with excess phosphorus oxychloride to produce 2-chloro-5-nitrobenzenesulfonic acid chloride. Obtain a slurry (first stage reaction). Next, when recovering excess phosphorus oxychloride, a specific organic medium is added as a replacement solvent, and then the phosphorus oxychloride is distilled off. Subsequently, the slurry of 2-chloro-5-nitrobenzenesulfonic acid chloride obtained here is amidated with aqueous ammonia to synthesize 2-chloro-5-nitrobenzenesulfonamide (second stage reaction). The feature of the present invention is the use of a specific organic medium and the industrially excellent process that leads to a consistent reaction in an appropriate slurry state and smooth two-step combination depending on the use location. Specifically, after the first stage reaction, by using a specific organic medium as a replacement solvent for phosphorus oxychloride (which is also the solvent in the first stage reaction), after distilling off the phosphorus oxychloride, 2-chloro -5-nitrobenzenesulfonic acid chloride is prevented from solidifying. Furthermore, after the second stage reaction, it can be easily recovered and recycled by simply separating the phases from the liquid separated by centrifugation. The reaction formula in the present invention is assumed as follows. Organic media applicable to the present invention include glycol ethers or aliphatic, cycloaliphatic or aromatic hydrocarbons having a boiling point range of 120 to 300°C, specifically ethylene glycol diethyl ether, ethylene glycol dipropyl ether;
Petroleum fractions, dodecane, tetradecane; decahydronaphthalene, dicyclohexyl; xylene, cumene, etc. are exemplified. Furthermore, halides falling within the above range, such as tetrachloroethane, can also be used. Of these, the boiling point is approximately 200℃ economically.
Preferred are hydrocarbon petroleum fractions such as lubricating oils (commercially available) having The amount of organic medium used is selected so that the slurry concentration of the target liquid is appropriate (approximately 30%).
A suitable amount is 2 to 4 times the weight of sodium chloro-5-nitrobenzenesulfonate. Note that when this organic medium is directly used in the first stage reaction, the reaction does not proceed at all and is not possible. Each reaction in the present invention is a solid-liquid reaction centered on solids, which is complicated and involves troublesome problems in terms of industrial technology, but the following operating conditions are usually adopted. In the first stage reaction, the appropriate amount of phosphorus oxychloride to be used is 5 to 10 moles (excess) to the raw material sodium 2-chloro-5-nitrobenzenesulfonate. The temperature is reflux (approximately 110° C.). In the second stage reaction, the appropriate amount of dilution water to be used is the same volume as that of the target solution, and the remaining phosphorus oxychloride is completely eliminated. Furthermore, the amount of ammonia water used is 5 to 5 to
A 10-fold molar excess (excess) is appropriate. The temperature is reflux (approximately 110° C.). The thus obtained crude liquid containing the target product 2-chloro-5-nitrobenzenesulfonamide is manufactured into a product by washing with water and drying according to a conventional method. If necessary, a product of higher quality can be obtained by treatment with activated carbon, recrystallization with methanol, or the like. EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples and Comparative Examples, but the present invention is not limited thereto. Example 1 Using a 500 ml flask with a stirrer, add 50 ml of sodium 2-chloro-5-nitrobenzenesulfonate.
g (0.193 mol) and 200 g (1.32 mol) of phosphorus oxychloride
20 mol) under reflux (approximately 110°C) on an oil bath.
heated for an hour. After the reaction, 100 g of hydrocarbon petroleum fraction (boiling point 200-260°C) (lubricating oil manufactured by Company A) was added as an organic medium.
Excess phosphorus oxychloride is distilled off (recovered) by reheating.
did. Subsequently, after diluting with 300 g of water, 80 g (1.08 mol) of 23% aqueous ammonia was added and heated under reflux (approximately 110° C.) on an oil bath for 30 minutes. Next, after cooling, it was filtered and washed with water according to the usual method, and further dried under reduced pressure at 100°C for 8 hours to form pale yellow crystals.
37 g (0.156 mol) were obtained. (Yield 80.8%) This crystal was found to be 2-chloro-5 by mass spectrometry and H-NMR.
- Confirmed to be nitrobenzenesulfonamide. Comparative Example 1 According to the method described in JP-A-58-65884 (without organic medium), 50 g (0.429 mol) of chlorosulfonic acid was added to 10 g (0.042 mol) of 2-chloro-5-nitrobenzenesulfonic acid. The reaction was allowed to proceed for 5 hours. After that, pour it into 500g of ice water and add 2-chloro-5.
-Nitrobenzene chloride was obtained. Next, add 10g of 28% ammonia water to the separated slag.
(0.165 mol) was added and reacted for 1 hour. rear,
Separation and drying yielded 4.4 g (0.019 mol) of 2-chloro-5-nitrobenzenesulfonamide. (Yield: 44.3%) This method involves injecting chlorosulfonic acid, which is a water-prohibited substance, into ice water, which is extremely dangerous both in the laboratory and industrially.
Moreover, the yield is very low. Comparative Example 2 In Example 1, the hydrocarbon petroleum fraction was
Although the same operation was carried out by adding it before the start of the stage reaction, the desired 2-chloro-5-nitrobenzenesulfonamide could not be obtained. Examples 2 to 4 The same operations as in Example 1 were performed except that 200 g of the compound shown in Table 1 was used as the organic medium, and the following results (Table 1) were obtained. 【table】
Claims (1)
ナトリウムを、過剰のオキシ塩化リンで２−クロ
ル−５−ニトロベンゼンスルホン酸クロライドと
し、次に有機媒体として、沸点範囲120〜300℃を
有するグリコールエーテル又は脂肪族、脂環式あ
るいは芳香族の炭化水素を加えた後、過剰のオキ
シ塩化リンを留去、置換し、続いて、アンモニア
水で反応することを特徴とする２−クロル−５−
ニトロベンゼンスルホンアミドの製造方法。1 Sodium 2-chloro-5-nitrobenzenesulfonate is converted to 2-chloro-5-nitrobenzenesulfonic acid chloride with excess phosphorus oxychloride, then as organic medium glycol ether or aliphatic with a boiling point range of 120-300 °C 2-chloro-5-, which is characterized in that after adding an alicyclic or aromatic hydrocarbon, excess phosphorus oxychloride is distilled off and replaced, and then reacted with aqueous ammonia.
Method for producing nitrobenzenesulfonamide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8985084A JPS60233051A (en) | 1984-05-04 | 1984-05-04 | Production of 2-chloro-5-nitrobenzenesulfonamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8985084A JPS60233051A (en) | 1984-05-04 | 1984-05-04 | Production of 2-chloro-5-nitrobenzenesulfonamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60233051A JPS60233051A (en) | 1985-11-19 |
| JPH045667B2 true JPH045667B2 (en) | 1992-02-03 |
Family
ID=13982250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8985084A Granted JPS60233051A (en) | 1984-05-04 | 1984-05-04 | Production of 2-chloro-5-nitrobenzenesulfonamide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60233051A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9046860B2 (en) | 1995-03-27 | 2015-06-02 | Canon Kabushiki Kaisha | Coupling part, photosensitive drum, process cartridge and electrophotographic image forming apparatus |
-
1984
- 1984-05-04 JP JP8985084A patent/JPS60233051A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9046860B2 (en) | 1995-03-27 | 2015-06-02 | Canon Kabushiki Kaisha | Coupling part, photosensitive drum, process cartridge and electrophotographic image forming apparatus |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60233051A (en) | 1985-11-19 |
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