JPS58172376A - Preparation of 5-ethyluracil - Google Patents
Preparation of 5-ethyluracilInfo
- Publication number
- JPS58172376A JPS58172376A JP57055615A JP5561582A JPS58172376A JP S58172376 A JPS58172376 A JP S58172376A JP 57055615 A JP57055615 A JP 57055615A JP 5561582 A JP5561582 A JP 5561582A JP S58172376 A JPS58172376 A JP S58172376A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- acid
- strong acid
- cyanobutyrylurea
- alpha
- 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.)
- Pending
Links
Abstract
Description
【発明の詳細な説明】
本発明は５−エチルウラノルの製造方法に関するもので
ある。さらに詳しくは１本発明はα−）７ノブチリル尿
素を強酸の存在にお−１で、接触還元することを特徴と
する５−エチルウラシルの製造方法に関するものである
。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing 5-ethyluranol. More specifically, the present invention relates to a method for producing 5-ethyluracil, which comprises catalytically reducing α-)7butyryl urea in the presence of a strong acid.
５−エチルウラノルはそれ自身、または、その誘導体の
生理活性から、医薬としての有用性が注目されている化
合物である。その製造方法につ０てはたとえば、フォノ
・メルカノノ、ベリヒテ第５２巻、８６９〜８８０貞Ｉ
１９１９年）によれば、７０ノ酸エステルから出発し
て、６エ程の煩雑な反応を経てようやく合成しており、
とても工業的製造に堪えるものではな（１゜また、ギュ
イヨー、メノツェル、コノトラップ、第２４６巻、４８
６〜４３８頁ＦｌＱ５８年）″ｆｔ力ルアブストラクソ
第５２巻、 １２８５０頁ｆ １９５８年〕、ギュイ
ヨー、ノヨパノ、メノソエル、プレタノ拳ノノエテ・デ
ュ・ノ２−デメフラノス１９６０年１５９６〜１６０２
頁、８７ミ力ルアブストラクツ第５５巻、 ＋１４２
７頁ｆ１９６１年）によれば、５−エチルウラノルを銅
粉の存在でキノリノ中で高温に加熱して合成して０るが
、この原料の調製が煩雑であるのみならず、高温の加熱
反応によって副生する不純物の除去が木蝋で、製品の品
質がよくなｔ１ヒ憂ζ収率もすぐれな（１゜さらに、ギ
ュナール他、８７ミカルアブストラクノ、第７０巻。5-ethyluranol is a compound that has attracted attention as a useful drug as a pharmaceutical because of the physiological activity of itself or its derivatives. Regarding the manufacturing method, see, for example, Fono Mercanono, Berichte Vol. 52, 869-880 Tei I
(1919), starting from 70 amino acid esters, it was finally synthesized after six complicated reactions.
It is not suitable for industrial production.
6-438 pages FlQ58)''ft Power Abstraxo Vol. 52, 12850 pages f 1958], Guyot, Noyo Pano, Meno Soel, Pretano Fist No Noete du No 2-Demefranos 1960 1596-1602
Page, 87 Milliful Abstracts Volume 55, +142
7, p. 1961), 5-ethyluranol is synthesized by heating it to high temperature in quinolino in the presence of copper powder, but not only is the preparation of this raw material complicated, but it is also synthesized by heating reaction at high temperature. By-product impurities are removed by using wax, and the quality of the product is good, and the yield is also excellent (1゜Furthermore, Günal et al., 87 Mical Abstracts, Vol. 70).
４００６ ｔ １９６９年） ｌζよれば、エチルα−
フィル芝ルブチレートを発煙硫酸中で尿素と反応させて
合成しているが、乙の方法にお０ても、原料の調製が面
倒であるし、製品の収率もよくな−１゜そこで１本発明
者は、５−エチルウラノルの工業的製造方法を確江すべ
く検Ｊｊシた結果、α−ノアノブチリル尿素を強酸の存
在下１こ接触還元したところ、驚くべきことに橋のて高
収率で高品位の５−エチルウラノルが得られることを見
出し１本発明を完成しｔこ。4006 t 1969) According to lζ, ethyl α-
Filthorn rubyrate is synthesized by reacting it with urea in fuming sulfuric acid, but even with the above method, the preparation of the raw materials is troublesome and the product yield is not good. The inventor conducted an investigation to establish an industrial method for producing 5-ethyluranol, and surprisingly, when α-noanobutyryl urea was catalytically reduced in the presence of a strong acid, a high yield was obtained. They discovered that high-grade 5-ethyluranol could be obtained and completed the present invention.
本発明方法にお−）て出発原料として用いるα−ノアノ
ブチリル尿素は。α-Noanobutyryl urea used as a starting material in the method of the present invention is as follows.
ノアノ酢酸エステルとアセトアルデヒドをパラジウム触
媒の存在下に接触還元の条件で縮合させて、まずα−ノ
アノ酪酸エステルを合成（アレキサノダー、コープ、オ
ルガニノクノノセノス１合冊第３ 、３８５〜６頁）し
。First, α-noanobutyric acid ester was synthesized by condensing noanoacetate and acetaldehyde under catalytic reduction conditions in the presence of a palladium catalyst (Alexanodar, Cope, Organinochnonocenos 1 Volume 3, pp. 385-6). .
これを鹸化し１こ後、尿１と縮合させること１こより、
融点１８１’の結晶として収率よく得られるに３ノノノ
、ノヨノズ１．；ヤーナルオブノ（イオロレカル’７ｉ
Ｘト’Ｊ−１第１巻、 ３０５−３１８頁）。After saponifying this and condensing it with urine,
Obtained in good yield as crystals with a melting point of 181', 3 nonono and 1. ；Yarnalobuno (Iororekal'7i
Xto'J-1 Vol. 1, pp. 305-318).
本発明ζこより５−エチルウラノルがクリられる過程を
反応式で示すと次のとおりである。The process by which 5-ethyluranol is purified by ζ of the present invention is shown in the following reaction formula.
強酸の存在により、常圧下で円滑に反応がすすみ、副生
成物の生成カ・認められず、略別の精製操作ないこＡ１
品位の５−エチルウラノルカ；取？得できろ−
本発明方法を実施するに際しては、１１１元触媒として
は、パラジウム系まｔこは白金系等の耐酸性の触媒が適
当であり、たとえば、５Φパラジウム−炭素を使用する
場合、１９１に対し、５０分の１ｖｋｌｌｉ！唄の使用
で室Ｍ、常圧１ζわＬｌて短時！Ｉｌｌ ｌこＩＩ！元
反応を完結させることができる。ｙ九反Ｌｒ終ｒ後、混
１墾を１げると閉環反応が効率よく進行する。そのＵｌ
ｌｌはｌｏｏ’ｃまてでト分である。Due to the presence of a strong acid, the reaction proceeds smoothly under normal pressure, and no by-products are produced.
The quality of 5-ethyluranorca; Tori? When carrying out the method of the present invention, acid-resistant catalysts such as palladium-based or platinum-based catalysts are suitable as the 111 primary catalyst. For example, when using 5Φ palladium-carbon, 191 On the other hand, 1/50th vklli! By using the song, the room M, normal pressure 1ζwa Ll is shortened! Ill lko II! The original reaction can be completed. After the completion of y, the ring-closing reaction proceeds efficiently by adding a mixture of 1 and 1. That Ul
ll is up to loo'c.
次に実施例を挙げて本発明方法をさらに説明する。Next, the method of the present invention will be further explained with reference to Examples.
（実施例）
α−ノアノブチリル尿素６０ｇ、水４５０ｄ、 濃塩酸
６８層ｌわよび５ ｅｐｔｙ ｒ （ラノウムー炭素１
２９をフラスコに仕込み、８ｒに加温し、これに水素ガ
スを注入し気液の接触をよくするためはげしくかき混ぜ
る。２時間で当モルの水素が吸収されｆコ。内谷をろ過
して柚媒を回収し、ろ液を８５〜９σに１ｌｔｌＵ、１
時間かき屍ぜて反応を終！する。デに冷やし、析出しｔ
こ結品をろ過、乾燥する。(Example) 60 g of α-noanobutyryl urea, 450 d of water, 68 layers of concentrated hydrochloric acid and 5 epty
29 was placed in a flask, heated to 8R, hydrogen gas was injected into it, and the mixture was stirred vigorously to improve gas-liquid contact. The equivalent mole of hydrogen is absorbed in 2 hours. Filter the Uchitani to collect the yuzu medium, and reduce the filtrate to 85-9σ by 1ltlU and 1
Take your time and finish the reaction! do. Cool and precipitate
Filter and dry the condensate.
５−′ｒ−チルウラノルの収率８７％。Yield of 5-'r-tyluranor 87%.
１１＠クロマトグラフにかけたが、不純物のスｆグトは
認められなかつｆこ。11 I applied it to a chromatograph, but no impurities were found.
紫外吸収スペクトル（メタノール中） λｍａス ２
６屯５ｎｍｌｏｇε λ９２Ultraviolet absorption spectrum (in methanol) λmas 2
6 tons 5 nm logε λ92
Claims (1)
還元することを特徴とする５−エチルウラノルの製造方
法。A method for producing 5-ethyluranol, which comprises catalytically reducing α-noanobutyryl urea in the presence of a strong acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57055615A JPS58172376A (en) | 1982-04-02 | 1982-04-02 | Preparation of 5-ethyluracil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57055615A JPS58172376A (en) | 1982-04-02 | 1982-04-02 | Preparation of 5-ethyluracil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS58172376A true JPS58172376A (en) | 1983-10-11 |
Family
ID=13003676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57055615A Pending JPS58172376A (en) | 1982-04-02 | 1982-04-02 | Preparation of 5-ethyluracil |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58172376A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5359248A (en) * | 1990-10-12 | 1994-10-25 | Seiko Epson Corporation | Corrosion resistant rotor with auxiliary yokes |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5686172A (en) * | 1979-12-15 | 1981-07-13 | Yodogawa Seiyaku Kk | Preparation of uracil |
-
1982
- 1982-04-02 JP JP57055615A patent/JPS58172376A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5686172A (en) * | 1979-12-15 | 1981-07-13 | Yodogawa Seiyaku Kk | Preparation of uracil |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5359248A (en) * | 1990-10-12 | 1994-10-25 | Seiko Epson Corporation | Corrosion resistant rotor with auxiliary yokes |
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