JPH04112879A - Production of 2-oxazolidone derivative by fixation of carbon dioxide using iron-sulfur complex - Google Patents
Production of 2-oxazolidone derivative by fixation of carbon dioxide using iron-sulfur complexInfo
- Publication number
- JPH04112879A JPH04112879A JP2231281A JP23128190A JPH04112879A JP H04112879 A JPH04112879 A JP H04112879A JP 2231281 A JP2231281 A JP 2231281A JP 23128190 A JP23128190 A JP 23128190A JP H04112879 A JPH04112879 A JP H04112879A
- Authority
- JP
- Japan
- Prior art keywords
- carbon dioxide
- formula
- iron
- sulfur complex
- substituted
- 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.)
- Granted
Links
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 229910002092 carbon dioxide Inorganic materials 0.000 title claims abstract description 21
- 239000001569 carbon dioxide Substances 0.000 title claims abstract description 21
- MBMLMWLHJBBADN-UHFFFAOYSA-N Ferrous sulfide Chemical compound [Fe]=S MBMLMWLHJBBADN-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 102000005298 Iron-Sulfur Proteins Human genes 0.000 title claims abstract description 10
- 108010081409 Iron-Sulfur Proteins Proteins 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical class O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 title claims description 5
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 20
- -1 aromatic thiol Chemical class 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 150000001412 amines Chemical class 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 9
- 150000002169 ethanolamines Chemical class 0.000 abstract description 8
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 4
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 abstract description 4
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 abstract description 4
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 150000003573 thiols Chemical class 0.000 description 5
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 238000006479 redox reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- AXBVSRMHOPMXBA-UHFFFAOYSA-N 4-nitrothiophenol Chemical compound [O-][N+](=O)C1=CC=C(S)C=C1 AXBVSRMHOPMXBA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- QCJQWJKKTGJDCM-UHFFFAOYSA-N [P].[S] Chemical compound [P].[S] QCJQWJKKTGJDCM-UHFFFAOYSA-N 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、化学的に二酸化炭素を固定化することにより
２−オキサシリドン誘導体を製造する方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing 2-oxacylidone derivatives by chemically fixing carbon dioxide.
二酸化炭素は炭素資源の最終酸化物であるが、地球上で
は植物等による炭酸同化作用によって、大気中の二酸化
炭素の増加が抑えられている。Carbon dioxide is the final oxide of carbon resources, and on Earth, the increase in atmospheric carbon dioxide is suppressed by carbon dioxide assimilation by plants and other organisms.
しかし、近年、エネルギー消費量の増加や森林破壊等に
よる二酸化炭素濃度の増加及びそれによって引き起こさ
れる地球温暖化か深刻な問題となってきている。そのた
めには、二酸化炭素を固定化する必要かあるが、この場
合、生成物は付加価値の高いものが望ましい。本発明で
は、二酸化炭素を２−オキサゾリドン誘導体として固定
化するか、この化合物は抗けいれん剤等の医薬品の原料
、中間体としての利用か考えられる。従来、２−オキサ
シリドン誘導体の製造は、エタノールアミンと炭酸ジエ
チル、クロル炭酸エチル又はホスゲンを作用させて得る
方法や有機アンチモン触媒を用いてエタノールアミン誘
導体と二酸化炭素から直接合成する方法等が考えられて
きた。However, in recent years, increased energy consumption, increased carbon dioxide concentration due to deforestation, and the resulting global warming have become serious problems. For this purpose, it is necessary to fix carbon dioxide, but in this case, it is desirable that the product has high added value. In the present invention, carbon dioxide may be immobilized as a 2-oxazolidone derivative, or this compound may be used as a raw material or intermediate for pharmaceuticals such as anticonvulsants. Conventionally, methods for producing 2-oxacylidone derivatives have been considered, such as a method in which ethanolamine is reacted with diethyl carbonate, ethyl chlorocarbonate, or phosgene, or a method in which 2-oxacylidone derivatives are directly synthesized from ethanolamine derivatives and carbon dioxide using an organic antimony catalyst. Ta.
しかしながら、ホスゲンのような試薬は毒性か極めて高
いという欠点がある。また、有機アンチモン触媒を用い
る系では、高温、高圧を必要とするという欠点かあった
。However, reagents such as phosgene have the disadvantage of being extremely toxic. Furthermore, systems using organic antimony catalysts had the disadvantage of requiring high temperatures and pressures.
本発明は、常温、常圧で、毒性の低い試薬を用いて二酸
化炭素を固定化することにより２−オキサシリドン誘導
体を製造する方法を提供することを目的とする。An object of the present invention is to provide a method for producing 2-oxacylidone derivatives by fixing carbon dioxide using a less toxic reagent at room temperature and pressure.
本発明の２−オキサゾリドン誘導体の製造方法は、
次式： ＦｅａＳ４（Ｃ５Ｈ５）４
て示される鉄−硫黄錯体、芳香族チオール、トリフェニ
ルホスフィン及び酸素の存在下、次式：
（式中、Ｒ１、Ｒ２、Ｒ３、及びＲ４はそれぞれ水素原
子、置換もしくは非置換の低級アルキル基又は置換もし
くは非置換のフェニル基を表わす。）で示されるエタノ
ールアミン誘導体と二酸化炭素を反応させることを特徴
とするものである。The method for producing a 2-oxazolidone derivative of the present invention includes the following formula: FeaS4(C5H5)4 In the presence of an iron-sulfur complex represented by FeaS4(C5H5)4, an aromatic thiol, triphenylphosphine, and oxygen, the following formula: (wherein R1, R2, R3, and R4 each represent a hydrogen atom, a substituted or unsubstituted lower alkyl group, or a substituted or unsubstituted phenyl group) and carbon dioxide are reacted. be.
すなわち、本発明は、シクロペンタジェニル環を配位子
とする４核鉄−硫黄錯体（ｐｅ４Ｓ４（ＣｓＨＳ）、）
を触媒とする芳香族チオールの酸化反応及びジスルフィ
ドとトリフェニルホスフィンとの酸化還元反応を駆動力
とする脱水縮合反応を利用して、エタノールアミン誘導
体と二酸化炭素を反応させることにより、２−オキサゾ
リドン誘導体を製造する方法を提供するものである。That is, the present invention provides a tetranuclear iron-sulfur complex (pe4S4 (CsHS)) having a cyclopentagenyl ring as a ligand.
A 2-oxazolidone derivative is produced by reacting an ethanolamine derivative with carbon dioxide using a dehydration condensation reaction using an oxidation reaction of an aromatic thiol as a catalyst and a redox reaction between a disulfide and triphenylphosphine as the driving force. The present invention provides a method for manufacturing.
本発明では、以下に示す反応サイクルが動くことによっ
て、二酸化炭素の固定化が達成される。In the present invention, fixation of carbon dioxide is achieved by the following reaction cycle.
（重置以下余白）
（２） ＋ ＲｓＰ＝Ｏ＋ Ａｒ５Ｈ
（重置以下余白）
（式中、Ａｒは芳香族基を、Ｒはフェニル基を表わし、
Ｒ１、Ｒ２、Ｒ３、及びＲ４は前記と同義である。）こ
の反応系において、まず鉄−硫黄錯体の酸化還元反応に
より酸素によるチオールの酸化か起こり、ジスルフィド
（ＡｒＳ−３Ａｒ）か生成する。(Margins below the overlapping position) (2) + RsP=O+ Ar5H (Margins below the overlapping position) (In the formula, Ar represents an aromatic group, R represents a phenyl group,
R1, R2, R3, and R4 have the same meanings as above. ) In this reaction system, thiol is first oxidized by oxygen through a redox reaction of the iron-sulfur complex, and disulfide (ArS-3Ar) is produced.
一方、エタノールアミン誘導体（１）と二酸化炭素は容
易に反応し、比較的安定なカルバメート（３）を生成す
る。また、ジスルフィドとトリフェニルホスフィン（Ｒ
３Ｐ）からは硫黄−リン中間体（４）か生成する。この
中間体（４）とカルバメート（３）は容易に反応し、中
間体（５）を生成する。更に、中間体（５）は分子内環
化反応を起こし、最終生成物（２−才キサシリドン誘導
体：２）となる。このとき、トリフェニルホスフィンは
不可逆的にトリフェニルホスフィンオキシト（Ｒ，Ｐ＝
ｏ）となり、またジスルフィドはチオールへ戻る。以上
のようにして、前記の反応サイクルか動く。On the other hand, the ethanolamine derivative (1) and carbon dioxide easily react to produce a relatively stable carbamate (3). In addition, disulfide and triphenylphosphine (R
3P) produces a sulfur-phosphorus intermediate (4). This intermediate (4) and carbamate (3) readily react to produce intermediate (5). Furthermore, the intermediate (5) undergoes an intramolecular cyclization reaction to become the final product (2-year-old xacylidone derivative: 2). At this time, triphenylphosphine is irreversibly converted to triphenylphosphine oxyto (R, P=
o), and the disulfide returns to a thiol. As described above, the reaction cycle described above operates.
前記式において、Ｒ１、Ｒ２、Ｒ３、又はＲ４で表わさ
れる低級アルキル基とは、炭素数１〜６の直鎖状又は分
枝状のアルキル基であり、例えばメチル基、エチル基、
プロピル基、イソプロピル基、ブチル基、イソブチル基
、５ｅＣ−ブチル基、ｔｅｒｔ−ブチル基、ペンチル基
、ヘキシル基か挙げられ、これらの低級アルキル基は、
例えば、ハロゲンなどて置換されていてもよい。また、
Ｒ１，Ｒ２、Ｒ３、又はＲ４て表わされるフェニル基は
、例えば、ハロゲンなとて置換されていてもよい。In the above formula, the lower alkyl group represented by R1, R2, R3, or R4 is a linear or branched alkyl group having 1 to 6 carbon atoms, such as a methyl group, an ethyl group,
These lower alkyl groups include propyl group, isopropyl group, butyl group, isobutyl group, 5eC-butyl group, tert-butyl group, pentyl group, and hexyl group.
For example, it may be substituted with halogen. Also,
The phenyl group represented by R1, R2, R3, or R4 may be substituted with, for example, halogen.
本発明に用いる芳香族チオールとしては、例えば２−メ
ルカプトピリジン、チオフェノール、４−ニトロチオフ
ェノールか挙げられる。また、反応溶媒はＮ、Ｎ−ジメ
チルホルムアミド（ＤＭＦ）のような非プロトン性溶媒
を使用する。Examples of the aromatic thiol used in the present invention include 2-mercaptopyridine, thiophenol, and 4-nitrothiophenol. Further, the reaction solvent used is an aprotic solvent such as N,N-dimethylformamide (DMF).
本発明における反応は、第三級アミンの存在下で行うこ
とか好ましい。チオールは解離型の方か酸化されやすい
ため、第三級アミンはチオールの中和剤として用いてい
る。第三級アミンとしては、トリエチルアミンなどが使
用できる。The reaction in the present invention is preferably carried out in the presence of a tertiary amine. Since thiol is more easily oxidized in its dissociated form, tertiary amines are used as thiol neutralizers. Triethylamine and the like can be used as the tertiary amine.
第三級アミンの使用量は、エタノールアミン誘導体（１
）の１，５倍程度か好ましい。また、鉄−硫黄錯体ｐｅ
４Ｓ４（Ｃ５Ｈ５）４の量はエタノールアミン誘導体の
３〜６％（モル％）程度か好ましい。トリフェニルホス
フィンはエタノールアミン誘導体と等モル量、チオール
は１１５モル量程度用いることか好ましい。本反応系に
おいて、鉄−硫黄錯体Ｆｅ４Ｓ４（Ｃ５Ｈ５）４の代わ
りにフェロセンを用いたり、また触媒を何も添加してい
ない系では、化合物（２）はほとんど生成しない。The amount of tertiary amine used is ethanolamine derivative (1
) is preferably about 1.5 times. In addition, iron-sulfur complex pe
The amount of 4S4(C5H5)4 is preferably about 3 to 6% (mol%) of the ethanolamine derivative. It is preferable to use triphenylphosphine in an equimolar amount to the ethanolamine derivative, and to use thiol in an amount of about 115 molar. In this reaction system, when ferrocene is used instead of the iron-sulfur complex Fe4S4(C5H5)4, or when no catalyst is added, compound (2) is hardly produced.
次に本発明を実施例により、更に詳細に説明する。 Next, the present invention will be explained in more detail with reference to Examples.
実施例
二酸化炭素を吹き込みなから、鉄−硫黄錯体Ｆｅ４Ｓ４
（Ｃ５Ｈ５）４（７，７ｍｇ）をＤＭＦ（４ｍｌ）に攪
拌しながら溶解した（約３０分）。次に、２−アミノ−
１−フェニルエタノール（２７，４ｍｇ）とトリエチル
アミン（４１μｌ）を加え、更に３０分間二酸化炭素を
吹き込んだ。最後に、トリフェニルホスフィン（０，４
ＭのＤＭＦ溶液０．５ｍ１）と２−メルカプトピリジン
（０，０８ＭのＤＭＦ溶液０．５ｍ１）を添加し、酸素
／二酸化炭素（約ｌ：２）の雰囲気下、２５°Ｃて攪拌
しなから反応させた。生成する５−フェニル−２−オキ
サシリドンは、高速液体クロマトグラフィー（ＯＤＳカ
ラムを使用：展開溶媒：水／アセトニトリル＝ ６０／
４０）で定量した。収率は、反応時間２２時間で約５０
％であった。Example: Iron-sulfur complex Fe4S4 without blowing carbon dioxide
(C5H5)4 (7.7 mg) was dissolved in DMF (4 ml) with stirring (approximately 30 minutes). Next, 2-amino-
1-phenylethanol (27.4 mg) and triethylamine (41 μl) were added, and carbon dioxide was further blown in for 30 minutes. Finally, triphenylphosphine (0,4
Add 2-mercaptopyridine (0.5 ml of 0.08 M DMF solution) and 2-mercaptopyridine (0.5 ml of 0.08 M DMF solution) under an atmosphere of oxygen/carbon dioxide (approximately 1:2) at 25 °C with stirring. Made it react. The generated 5-phenyl-2-oxacylidone was purified by high performance liquid chromatography (using an ODS column: developing solvent: water/acetonitrile = 60/
40). The yield is approximately 50% with a reaction time of 22 hours.
%Met.
本発明によれば、常温、常圧で、毒性の低い試薬を用い
ることにより、大気中の二酸化炭素濃度を減少させて地
球温暖化を防ぐとともに、付加価値の高い物質である２
−オキサシリドン誘導体を製造することかできる。According to the present invention, by using a reagent with low toxicity at room temperature and normal pressure, the concentration of carbon dioxide in the atmosphere can be reduced and global warming can be prevented, and the substance has high added value.
- Oxacylidone derivatives can be produced.
Claims (1)
れる鉄−硫黄錯体、芳香族チオール、トリフェニルホス
フィン及び酸素の存在下、次式： ▲数式、化学式、表等があります▼ （式中、Ｒ＾１、Ｒ＾２、Ｒ＾３、及びＲ＾４は、それ
ぞれ水素原子、置換もしくは非置換の低級アルキル基又
は置換もしくは非置換のフェニル基を表わす。）で示さ
れるエタノールアミン誘導体と二酸化炭素を反応させる
ことを特徴とする。 次式 ▲数式、化学式、表等があります▼ （式中、Ｒ＾１、Ｒ＾２、Ｒ＾３、及びＲ＾４は、前記
と同義である。）で示される２−オキサゾリドン誘導体
の製造方法。 ２、更に第三級アミンの存在下に反応を行う請求項１記
載の製造方法。[Claims] 1. In the presence of an iron-sulfur complex represented by the following formula: Fe_4S_4(C_5H_5)_4, an aromatic thiol, triphenylphosphine, and oxygen, the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R^1, R^2, R^3, and R^4 each represent a hydrogen atom, a substituted or unsubstituted lower alkyl group, or a substituted or unsubstituted phenyl group.) It is characterized by reacting an amine derivative with carbon dioxide. Production of a 2-oxazolidone derivative represented by the following formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R^1, R^2, R^3, and R^4 have the same meanings as above.) Method. 2. The manufacturing method according to claim 1, wherein the reaction is further carried out in the presence of a tertiary amine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2231281A JPH0649691B2 (en) | 1990-08-31 | 1990-08-31 | Method for producing 2-oxazolidone derivative by carbon dioxide fixation using iron-sulfur complex |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2231281A JPH0649691B2 (en) | 1990-08-31 | 1990-08-31 | Method for producing 2-oxazolidone derivative by carbon dioxide fixation using iron-sulfur complex |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04112879A true JPH04112879A (en) | 1992-04-14 |
| JPH0649691B2 JPH0649691B2 (en) | 1994-06-29 |
Family
ID=16921147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2231281A Expired - Lifetime JPH0649691B2 (en) | 1990-08-31 | 1990-08-31 | Method for producing 2-oxazolidone derivative by carbon dioxide fixation using iron-sulfur complex |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0649691B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013199456A (en) * | 2012-03-26 | 2013-10-03 | Nagoya Univ | Method for producing annular urethane |
-
1990
- 1990-08-31 JP JP2231281A patent/JPH0649691B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013199456A (en) * | 2012-03-26 | 2013-10-03 | Nagoya Univ | Method for producing annular urethane |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0649691B2 (en) | 1994-06-29 |
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