JPS58121257A - N,n'-ditroponyl-oxa- or thia-diaminoalkane - Google Patents
N,n'-ditroponyl-oxa- or thia-diaminoalkaneInfo
- Publication number
- JPS58121257A JPS58121257A JP448582A JP448582A JPS58121257A JP S58121257 A JPS58121257 A JP S58121257A JP 448582 A JP448582 A JP 448582A JP 448582 A JP448582 A JP 448582A JP S58121257 A JPS58121257 A JP S58121257A
- Authority
- JP
- Japan
- Prior art keywords
- oxa
- compound
- thia
- useful
- diaminoalkane
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、有用な新規金属キレート剤、ビスシクロへブ
タトリエノ−テトラアザ−ジオキサ又はンチアーシクロ
アルケンの合成過程において、重要な中間体となるN
−N’−シトロボニル−オキサ又はチア−ジアミノアル
カンに関する。DETAILED DESCRIPTION OF THE INVENTION The present invention provides a useful new metal chelating agent, N, which is an important intermediate in the synthesis process of biscyclohebutatrieno-tetraaza-dioxa or anticycloalkene.
-N'-citrobonyl-oxa or thia-diaminoalkane.
従来、廃水等からの重金属の除去、人体内の重金属の無
毒化、除去または海水からのウラン等有用金属の回収な
どを行なうために、多くの金属キレート剤が開発されて
きた。Conventionally, many metal chelating agents have been developed to remove heavy metals from wastewater, detoxify or remove heavy metals from the human body, or recover useful metals such as uranium from seawater.
かかる観点から、本発明者らは、先に下r一般式〔1〕
に表わされる2−アルキルアミノトロポンイミンダイマ
ーを有用な金属キレート剤として発明している。From this point of view, the present inventors first prepared the following general formula [1]
The 2-alkylaminotroponimine dimer represented by is invented as a useful metal chelating agent.
ここでk及びlは、それぞれlO以下の整数を表わす。Here, k and l each represent an integer less than or equal to lO.
しかし、これにさらに金^選択性を与えることを目的と
し、鋭意研究を重ねた結果、有用な金属キレート剤、ビ
スシクロヘプタトリエノ−テトラアザ−ジオキサ又はジ
チア−シクロアルケンを発明するに至夛、その合成過程
において、重要な中間体である本発明の化合物を見い出
したものである0
本発明の化合物は、新規な化合物であシ、本発明者らに
よって初めて合成されたものである。また、ビスシクロ
へブタトリエノ−テトラアザ−ジオキサ又はジチア−シ
クロアルケンのみならず、種々の有機化合物を合成する
ための中間体としても、非常に有用である。However, as a result of intensive research with the aim of imparting further gold selectivity to this, we were able to invent a useful metal chelating agent, biscycloheptatrieno-tetraaza-dioxa or dithia-cycloalkene. In the synthesis process, the compound of the present invention, which is an important intermediate, was discovered.The compound of the present invention is a novel compound, and was synthesized for the first time by the present inventors. Moreover, it is very useful not only as biscyclohebutatrieno-tetraaza-dioxa or dithia-cycloalkene but also as an intermediate for synthesizing various organic compounds.
本発明の化合物は、下記一般式〔2〕で表わされる。The compound of the present invention is represented by the following general formula [2].
ここでAは酸累又は硫黄を、m、nはそれぞれ2〜4の
整数を表わす。また塩とは、塩酸塩、臭化水素酸塩、硫
酸塩、硝酸塩等の無機酸の塩、及び酢酸塩等の有機酸の
塩など、通常の条件下でアミ7基と結合する酸との塩を
いう。Here, A represents an acid compound or sulfur, and m and n each represent an integer of 2 to 4. In addition, salts include salts of inorganic acids such as hydrochloride, hydrobromide, sulfate, and nitrate, and salts of organic acids such as acetate. Refers to salt.
以下、いくつかの代表的化合物について、その合成法及
び物性を示す。The synthesis methods and physical properties of some representative compounds are shown below.
ア、 N% N′−ジー(2−トロボニル)−3−オキ
サ−1,5−ジアミノペンタ/
2−クロルトロボン(29071fi、9.20.7
m mole )、トリエチルアミン(2593WLg
、25.6 m mole )、3.−宇キサ−1,5
−ジアミノペンタンC14C14l4、ff3.6 m
mole)と無水エタノール(50ml)の混合物を
9.5時間加熱還流した。減圧濃縮後、クロロホルムに
溶かし、飽和重炭酸ナトリウム、水で洗滌、硫酸マグネ
シウムで乾燥、減圧濃縮して褐色オイル(3,31g)
を得た。これをシリカゲル(30g)でカラムクロマト
を行ない、クロロホルム−瑯酸エチルの留分よシ黄色固
体(2,24p)を得た。これを酢酸エチルよシ再結晶
して、黄色針状晶(1703Qs収率53チ)として目
的物を得た。A, N% N'-di(2-trobonyl)-3-oxa-1,5-diaminopenta/2-chlorotrobone (29071fi, 9.20.7
mmole), triethylamine (2593WLg
, 25.6 mmole), 3. -Ukisa-1,5
-diaminopentane C14C14l4, ff3.6 m
A mixture of mol) and absolute ethanol (50 ml) was heated under reflux for 9.5 hours. After concentration under reduced pressure, dissolve in chloroform, wash with saturated sodium bicarbonate, water, dry over magnesium sulfate, and concentrate under reduced pressure to obtain a brown oil (3.31 g).
I got it. This was subjected to column chromatography on silica gel (30 g) to obtain a yellow solid (2.24p) as a chloroform-ethyl ethylate fraction. This was recrystallized from ethyl acetate to obtain the desired product as yellow needles (1703Qs yield: 53%).
物性
融点 95.5〜97.2℃
”w−xMx (cDq13、δ値)
7.53〜7.08 (8H,、7L)、6.78〜6
.53 (4H%711L)、3.80 (4H,t、
J==eH2)、3.57 (4H’% (1% J
=6H2)
13C−NMR(CDC13、δ値)
176.54.155.39.137.05.136.
06.128.66.122.2’8,108.53.
68.81.42.43工R(OHC13溶液)
3320.1610.1595.1545.1515.
1455、 cm−’
元素分析 CI8’2003”2
理論値 a:69.21、H:6.45、N : 8.
97実測値 c:69.42、H:6.54、N:9.
09イ、 N、N’−ジー(2−トロボニル)−3−チ
ア−1,5−ジアミノペンタン
2−クロルトロボ/(2990+ng、21.3 m
mole )、トリエチルアミン(2295rng、2
2.7 m mole)、3−チア−1,5−ジアミノ
ペンタン(1414mg、11.8mmo1e)を無水
エタノール(5oml)に漕力・し8時間加熱還流した
。反応混合物を減圧濃縮後、残置をクロロホルムに溶か
し、飽和重炭酸ナトリウム、水で洗滌、無水硫酸マグネ
・/ラムで乾燥した。溶媒を減圧留去して得られた褐色
オイルをシリカゲル(60g)でカラムクロマトを行な
った。Physical properties Melting point 95.5-97.2°C "w-xMx (cDq13, δ value) 7.53-7.08 (8H, 7L), 6.78-6
.. 53 (4H%711L), 3.80 (4H,t,
J==eH2), 3.57 (4H'% (1% J
=6H2) 13C-NMR (CDC13, δ value) 176.54.155.39.137.05.136.
06.128.66.122.2'8,108.53.
68.81.42.43 Engineering R (OHC13 solution) 3320.1610.1595.1545.1515.
1455, cm-' Elemental analysis CI8'2003''2 Theoretical value a: 69.21, H: 6.45, N: 8.
97 actual measurement values c: 69.42, H: 6.54, N: 9.
09i, N, N'-di(2-trobonyl)-3-thia-1,5-diaminopentane 2-chlorotrobo/(2990+ng, 21.3 m
mole), triethylamine (2295 rng, 2
2.7 mmole) and 3-thia-1,5-diaminopentane (1414 mg, 11.8 mmole) were added to absolute ethanol (5 oml) and heated under reflux for 8 hours. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in chloroform, washed with saturated sodium bicarbonate and water, and dried over anhydrous magnesium sulfate/rum. The brown oil obtained by distilling off the solvent under reduced pressure was subjected to column chromatography on silica gel (60 g).
クロロホルム/酢酸エチル(20〜100%)留分より
得られた黄色オイル(2,4sl)をクロロホルム/酢
酸エチルより再結晶して黄色結晶(1856m9、収率
53チ)を得た0
物性
融点 127.5〜129.2℃
’H−NMR(CDC13、δ値)
7.49(2H%be)、7.41〜7.06 (6I
(、IrL)、6.79〜6.48 (4H,trL
)、3.57 (4L q、 J=7.0H2)、2.
91 (4H%t、 J=7.OHz )13a’−n
MR(cpcb、5値)
176.60,154.87.137.17.135.
00.128.92.122.54.108.45.4
2.25.30.61工R(OHC13溶液)
3310.1605.1597.1545.15o5.
1453、cIrL−’
MS(M/’Z)、328(M+)
分析 CI& Hzo N z OJ S遼論値 C;
69.11?3.H;6、+3. N5Ft期ワyy
@ c; 6g、Fb、 ト1; 6
.of、 N; &、33出願人A yellow oil (2.4 sl) obtained from a chloroform/ethyl acetate (20-100%) fraction was recrystallized from chloroform/ethyl acetate to obtain yellow crystals (1856 m9, yield 53 cm)0 Physical properties Melting point 127 .5-129.2°C 'H-NMR (CDC13, δ value) 7.49 (2H%be), 7.41-7.06 (6I
(, IrL), 6.79-6.48 (4H, trL
), 3.57 (4L q, J=7.0H2), 2.
91 (4H%t, J=7.OHz) 13a'-n
MR (cpcb, 5 values) 176.60, 154.87.137.17.135.
00.128.92.122.54.108.45.4
2.25.30.61 Engineering R (OHC13 solution) 3310.1605.1597.1545.15o5.
1453, cIrL-' MS (M/'Z), 328 (M+) Analysis CI & Hzo N z OJ S Liao logical value C;
69.11?3. H; 6, +3. N5Ft period yy
@c; 6g, Fb, t1; 6
.. of, N; &, 33 Applicant
Claims (1)
キサ又はチア−ジアミノアルカンおよびその塩。 ここでAは、酸素又は硫黄を、m、nはそれぞれ2〜4
の整数を表わす。[Scope of Claims] N-N'-citrobonyl-oxa or thia-diaminoalkane and salts thereof, represented by the following general formula. Here, A is oxygen or sulfur, and m and n are each 2 to 4.
represents an integer.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP448582A JPS58121257A (en) | 1982-01-13 | 1982-01-13 | N,n'-ditroponyl-oxa- or thia-diaminoalkane |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP448582A JPS58121257A (en) | 1982-01-13 | 1982-01-13 | N,n'-ditroponyl-oxa- or thia-diaminoalkane |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS58121257A true JPS58121257A (en) | 1983-07-19 |
Family
ID=11585392
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP448582A Pending JPS58121257A (en) | 1982-01-13 | 1982-01-13 | N,n'-ditroponyl-oxa- or thia-diaminoalkane |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS58121257A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001292855A (en) * | 2000-04-12 | 2001-10-23 | Delta Kogyo Co Ltd | Boolmer-type lumbar support device |
US8690255B2 (en) | 2010-06-04 | 2014-04-08 | Honda Motor Co., Ltd. | Seat back frame |
-
1982
- 1982-01-13 JP JP448582A patent/JPS58121257A/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001292855A (en) * | 2000-04-12 | 2001-10-23 | Delta Kogyo Co Ltd | Boolmer-type lumbar support device |
US8690255B2 (en) | 2010-06-04 | 2014-04-08 | Honda Motor Co., Ltd. | Seat back frame |
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