JPS585183B2 - Seizouhouhou - Google Patents
SeizouhouhouInfo
- Publication number
- JPS585183B2 JPS585183B2 JP3408474A JP3408474A JPS585183B2 JP S585183 B2 JPS585183 B2 JP S585183B2 JP 3408474 A JP3408474 A JP 3408474A JP 3408474 A JP3408474 A JP 3408474A JP S585183 B2 JPS585183 B2 JP S585183B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- compound
- hydrazine
- toluidine
- added
- 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
- 150000001875 compounds Chemical class 0.000 claims description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000000034 method Methods 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 5
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 5
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000002429 hydrazines Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- GORXOMQYBYURLM-UHFFFAOYSA-N 2-(n-ethyl-3-methyl-4-nitrosoanilino)ethanol Chemical compound OCCN(CC)C1=CC=C(N=O)C(C)=C1 GORXOMQYBYURLM-UHFFFAOYSA-N 0.000 description 2
- FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910000377 hydrazine sulfate Inorganic materials 0.000 description 2
- 239000012493 hydrazine sulfate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- IXKRLNGTKXUSEI-UHFFFAOYSA-N n,n-diethyl-3-methyl-4-nitrosoaniline Chemical compound CCN(CC)C1=CC=C(N=O)C(C)=C1 IXKRLNGTKXUSEI-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GVEYRUKUJCHJSR-UHFFFAOYSA-N (4-azaniumyl-3-methylphenyl)-ethyl-(2-hydroxyethyl)azanium;sulfate Chemical compound OS(O)(=O)=O.OCCN(CC)C1=CC=C(N)C(C)=C1 GVEYRUKUJCHJSR-UHFFFAOYSA-N 0.000 description 1
- XTBFKMDOQMQYPP-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine;hydron;chloride Chemical compound Cl.CCN(CC)C1=CC=C(N)C=C1 XTBFKMDOQMQYPP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- RAESLDWEUUSRLO-UHFFFAOYSA-O aminoazanium;nitrate Chemical compound [NH3+]N.[O-][N+]([O-])=O RAESLDWEUUSRLO-UHFFFAOYSA-O 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- OLNMJIHADFYHAK-UHFFFAOYSA-N n,n-diethyl-4-nitrosoaniline Chemical compound CCN(CC)C1=CC=C(N=O)C=C1 OLNMJIHADFYHAK-UHFFFAOYSA-N 0.000 description 1
- XWQURWIJAIIPQP-UHFFFAOYSA-N n-[2-(n-ethyl-3-methyl-4-nitrosoanilino)ethyl]methanesulfonamide Chemical compound CS(=O)(=O)NCCN(CC)C1=CC=C(N=O)C(C)=C1 XWQURWIJAIIPQP-UHFFFAOYSA-N 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 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、４−アミノ−Ｎ、Ｎ−ジアルキルアニリン類
（以下化合物Ｃと略称する。DETAILED DESCRIPTION OF THE INVENTION The present invention provides 4-amino-N,N-dialkylanilines (hereinafter abbreviated as compound C).
）の製法に関する。).
更に詳記すれば、Ｎ、Ｎ−ジアルキルアニリン類（以下
化合物Ａと略称する。More specifically, N,N-dialkylanilines (hereinafter abbreviated as compound A).
）を常法によってニトロソ化して得た、４−ニトロン−
Ｎ、Ｎ−ジアルキルアニリン類（以下化合物Ｂと略称す
る。) obtained by nitrosation of 4-nitrone-
N,N-dialkylanilines (hereinafter abbreviated as compound B).
）をヒドラジン類と反応させて還元し、化合物Ｃを取得
する方法に関する。) is reacted with hydrazines and reduced to obtain compound C.
化合物Ｃは、写真用現像薬、等にカラーペーパー関係の
現像薬として使用される。Compound C is used as a color paper-related developer, such as a photographic developer.
従来、化合物Ｂを経由して、化合物Ａを製造する方法と
しては、加圧下に触媒を用いて行う方法や、亜鉛末と塩
酸とによる還元方法が一般的な方法として知られていた
。Conventionally, as a method for producing compound A via compound B, a method using a catalyst under pressure and a reduction method using zinc dust and hydrochloric acid have been known as general methods.
しかしながら前者の方法は、高圧の為、高価にして容量
に制限のある設備、高価な触媒と過剰の水素、長時間を
要する操作などを必要とし、後者の方法は、反応成績体
よりの生成物の単離が非常に困難であり、その為収率は
低下し、廃液処理の点等についても問題があった為、い
ずれも工業的製造方法としては、採用し難かった。However, the former method requires high pressure, expensive equipment with limited capacity, expensive catalysts, excess hydrogen, and long operations, while the latter method requires products from the reaction product. It was very difficult to isolate, resulting in a low yield, and there were also problems with waste liquid treatment, so it was difficult to adopt any of these methods as an industrial production method.
本発明者等は、化合物Ｂを工業的に容易に製造する方法
を見出す為鋭意検討し、化合物Ｂをヒドラジン類で還元
することによって、着色の少ない製品を高収率で工業的
に容易に製造することの出来る、本発明方法を完成した
。The inventors of the present invention conducted extensive research to find a method for industrially producing Compound B, and by reducing Compound B with hydrazines, products with less coloring can be produced industrially and easily in high yield. We have completed the method of the present invention that allows this.
本発明に使用する化合物Ｂとは、一般式
（式中Ｒ１，Ｒ２はアルキル及び置換アルキルを、Ｒ３
は水素及び低級アルキル基を示す。Compound B used in the present invention has the general formula (wherein R1 and R2 are alkyl and substituted alkyl, R3
represents hydrogen and a lower alkyl group.
）なる化合物で、例えば、４−二トロンジメチルアニリ
ン、Ｎ−エチル−Ｎ−（ヒドロキシエチル）−４−ニト
ロソ−ｍ−トルイジン、４−二トロンジエチルアニリン
、４−ニトロソ−Ｎ、Ｎ−ジエチル−ｍ−トルイジン、
４−ニトロン−Ｎ−エチル−Ｎ−（メチルスルホンアミ
ドエチル）−ｍ−トルイジン等が挙げられる。), such as 4-nitrone dimethylaniline, N-ethyl-N-(hydroxyethyl)-4-nitroso-m-toluidine, 4-nitrone diethylaniline, 4-nitroso-N,N-diethyl- m-toluidine,
Examples include 4-nitrone-N-ethyl-N-(methylsulfonamidoethyl)-m-toluidine.
本発明方法は、例えば化合物Ｂを単独、又は原料と反応
しない有機溶剤に溶解して、ヒドラジン類と混じ、攪拌
反応させて反応を完結させればよい。In the method of the present invention, for example, Compound B may be used alone or dissolved in an organic solvent that does not react with the raw materials, mixed with hydrazines, stirred, and reacted to complete the reaction.
ヒドラジン類としては、通常抱水ヒドラジンを用いるが
、ヒドラジン、硫酸ヒドラジン、硝酸ヒドラジン等であ
ってもよい。As the hydrazine, hydrazine hydrate is usually used, but hydrazine, hydrazine sulfate, hydrazine nitrate, etc. may also be used.
ヒドラジン類の使用量は、理論量乃至理論の若干過剰量
用いればよい。The amount of hydrazine used may be a stoichiometric amount or a slight excess of the stoichiometric amount.
反応に当って有機溶剤を使用する場合には、アルコール
類、芳香族炭化水素類など化合物Ｂを溶解する通常の有
機溶剤が使用出来る。When an organic solvent is used in the reaction, ordinary organic solvents that dissolve compound B, such as alcohols and aromatic hydrocarbons, can be used.
反応温度は、常温乃至反応溶剤の還流する温度で行うの
が好ましい。The reaction temperature is preferably room temperature to reflux temperature of the reaction solvent.
化合物Ｃは通常塩酸塩、硫酸塩等として使用される。Compound C is usually used as a hydrochloride, sulfate, or the like.
これらの塩として単離するには、例えば、反応終了液よ
り溶媒で化合物Ｃを抽出し、抽出液にこれらの酸の水溶
液を加え、分液抜水層を濃縮して結晶を得る。To isolate these salts, for example, compound C is extracted from the reaction-completed solution with a solvent, an aqueous solution of these acids is added to the extract, and the separated aqueous layer is concentrated to obtain crystals.
以上述べた如く、本発明方法は、廃液処理の問題は全く
なく、大量仕込みが可能であり、操作が容易で、高品質
の製品が高収量で得られる等の利点を有する、工業的に
極めて価値の高いものであり、新米に貢献する所極めて
太きい。As mentioned above, the method of the present invention has advantages such as no problem with waste liquid treatment, large-scale preparation, easy operation, and high yield of high-quality products. It is of high value, and its contribution to new rice is extremely important.
以下に実施例を挙げ、本発明を更に説明する。The present invention will be further explained with reference to Examples below.
実施例中敷量を表わす部は重量部である。The parts representing the amount of insole in the examples are parts by weight.
実施例 １
Ｎ−エチル−Ｎ−（ヒドロキシエチル）−４−ニトロソ
−ｍ−トルイジン１２０部にベンゼン２００部を加えて
溶解させ、８０％抱水ヒドラジン４０部を、６０〜７０
℃１時間で滴下した。Example 1 200 parts of benzene was added to 120 parts of N-ethyl-N-(hydroxyethyl)-4-nitroso-m-toluidine and dissolved, and 40 parts of 80% hydrazine hydrate was added to 60 to 70 parts of hydrazine hydrate.
It was added dropwise at 1 hour.
同一温度で２時間反応後、５％硫酸１１００部で抽出し
、分液後濃縮乾固し、メタノールより再結晶してＮ−エ
チル−Ｎ−（ヒドロキシエチル）−４−アミノ−ｍ−ト
ルイジン硫酸塩１３３部を得た。After reacting for 2 hours at the same temperature, it was extracted with 1100 parts of 5% sulfuric acid, separated, concentrated to dryness, and recrystallized from methanol to give N-ethyl-N-(hydroxyethyl)-4-amino-m-toluidine sulfate. 133 parts of salt were obtained.
融点１５５〜１５６℃の白色晶であった。It was a white crystal with a melting point of 155-156°C.
実施例 ２
Ｎ、Ｎ−ジエチル−４−ニトロソ−ｍ−トルイジン９２
部に水２５０部と硫酸ヒドラジン１１０部と５０％カセ
イソーダ８０部を加える。Example 2 N,N-diethyl-4-nitroso-m-toluidine 92
250 parts of water, 110 parts of hydrazine sulfate, and 80 parts of 50% caustic soda are added to the solution.
５０〜６０℃で５時間反応後、トルエン１００部を加え
て抽出する。After reacting at 50-60°C for 5 hours, 100 parts of toluene is added for extraction.
抽出液より１０％塩酸１３０部で抽出し、分液後濃縮乾
固し、メタノールより再結晶し、Ｎ、Ｎ−ジエチル−４
−アミノ−ｍ−トルイジンのモノ塩酸塩９０部を得た。The extract was extracted with 130 parts of 10% hydrochloric acid, separated, concentrated to dryness, recrystallized from methanol, and N,N-diethyl-4
90 parts of monohydrochloride of -amino-m-toluidine was obtained.
融点２２４〜２２５℃の白色晶であった。It was a white crystal with a melting point of 224-225°C.
実施例 ３
Ｎ、Ｎ−ジエチル−４−ニトロソアニリン９０部にトル
エン１５０部を加えて溶解させ、８０％抱水ヒドラジン
４２部を７０〜８０℃１時間で滴下した。Example 3 150 parts of toluene was added to 90 parts of N,N-diethyl-4-nitrosoaniline to dissolve it, and 42 parts of 80% hydrazine hydrate was added dropwise at 70 to 80°C for 1 hour.
同一温度で１時間反応後、１０％塩酸１８０部で抽出し
、濃縮乾固後イソプロピルアルコールより再結晶して、
Ｎ、Ｎ−ジエチル−４−アミノアニリン塩酸塩８７部を
得た。After reacting at the same temperature for 1 hour, it was extracted with 180 parts of 10% hydrochloric acid, concentrated to dryness, and then recrystallized from isopropyl alcohol.
87 parts of N,N-diethyl-4-aminoaniline hydrochloride were obtained.
融点２２２〜２２３℃であった。The melting point was 222-223°C.
実施例 ４
４−ニトロソ−Ｎ−エチル−Ｎ−（メチルスルホンアミ
ドエチル）−ｍ−トルイジン１１５部に水１５０部を加
え、８０％抱水ヒドラジン４１部を８０〜９０℃１時間
で滴下した。Example 4 150 parts of water was added to 115 parts of 4-nitroso-N-ethyl-N-(methylsulfonamidoethyl)-m-toluidine, and 41 parts of 80% hydrazine hydrate was added dropwise at 80 to 90°C for 1 hour.
同一温度で２時間反応後、ジクロルメタン１５０部で抽
出し、水洗した抽出液から揮発分を留去し、融点９０〜
９２℃の化合物９３部を得た。After reacting at the same temperature for 2 hours, it was extracted with 150 parts of dichloromethane, and the volatile matter was distilled off from the water-washed extract.
93 parts of a compound at 92°C was obtained.
Claims (1)
２Ｈ４ＮＨ８Ｏ２ＣＨ３を、Ｒ３は水素、及び低級アル
キル基を示す。 ）なる化合物を、ヒドラジン類で還元することを特徴と
する、式 （式中Ｒ１、Ｒ２、Ｒ３は前記と同じ。 ）なる化合物の製造方法。[Claims] 1 General formula (wherein R1 and R2 are alkyl and -C2H40H2-C
2H4NH8O2CH3, R3 represents hydrogen and a lower alkyl group. ) A method for producing a compound of the formula (wherein R1, R2, and R3 are the same as above), which comprises reducing the compound with a hydrazine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3408474A JPS585183B2 (en) | 1974-03-27 | 1974-03-27 | Seizouhouhou |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3408474A JPS585183B2 (en) | 1974-03-27 | 1974-03-27 | Seizouhouhou |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS50129526A JPS50129526A (en) | 1975-10-13 |
| JPS585183B2 true JPS585183B2 (en) | 1983-01-29 |
Family
ID=12404382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3408474A Expired JPS585183B2 (en) | 1974-03-27 | 1974-03-27 | Seizouhouhou |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS585183B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115960002B (en) * | 2022-12-14 | 2025-01-28 | 江西凌富生物科技有限公司 | A method for reducing nitrosobenzene compounds |
-
1974
- 1974-03-27 JP JP3408474A patent/JPS585183B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50129526A (en) | 1975-10-13 |
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