BE606096A - - Google Patents
Info
- Publication number
- BE606096A BE606096A BE606096DA BE606096A BE 606096 A BE606096 A BE 606096A BE 606096D A BE606096D A BE 606096DA BE 606096 A BE606096 A BE 606096A
- Authority
- BE
- Belgium
- Prior art keywords
- desc
- hydrochloric acid
- benzol
- toluol
- pyridine
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 2
- 230000001131 transforming Effects 0.000 claims description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims 1
- 241001527806 Iti Species 0.000 claims 1
- 101710015094 MOCS2 Proteins 0.000 claims 1
- -1 alkyl radicals Chemical class 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- 210000003169 Central Nervous System Anatomy 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- FFLYUXVZEPLMCL-UHFFFAOYSA-N ethylchloranuidyl formate Chemical compound CC[Cl-]OC=O FFLYUXVZEPLMCL-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001624 sedative Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- NRTOMJZYCJJWKI-UHFFFAOYSA-N titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
EMI1.1
"Procède db prépara tion de ;=rirs de l'"cide carbamique substi-
EMI1.2
tués en N".
EMI1.3
Les ',';.,'.':"J ..L1;;;C::'U": crua.ùlCLiB 01: uréthsnes qui o..t pf)ur formule ,:-=ra7¯e
EMI1.4
EMI1.5
dans laquelle R1 et R représentent de l'hydrogène ou des radicau: alkyles, aryles ou pralkyles, et Rp et R3 des radicaux alkyles,
EMI1.6
aryles ou aralkyles, sont des produits chimiques non encore dé-
EMI1.7
crits. Les COI:1.Josés de ce cjrje e p# sèdent, à côté d'une f:.ible toxi cité dans l'essai pi:ar:nacola7iqae, des effets importants sur le
<Desc/Clms Page number 2>
système nerveux central. Four une partie de ces composes, l'activité sédative est particulièrement ::arquée.
EMI2.1
La préparation de l'uréthane :-(3=hydroxy-,z disubstïtué propyle) précité se fait en faisant réagir la 3-h;,rdroxyalkylamine correspondante avec du <;loroiorniate d'éthyle.
La transformation se fait df1ns un sc.lvpnt indifférent (par exemple benzol, toluol) en présence d'un accepteur d'acide chlorhydrique
EMI2.2
(par exemple triéthylsmine, pyridine, dinéthyë&ni-1-i-ne). On a trou- vé que la triéthylamine est l'accepteur d'acide chlorhydrique qui convient le mieux, parce que le chlorure bien cristallisé peut être éliminé du mélange de réaction sans difficulté. Apres avoir séparé le solvant, on obtient par distillation l'uréthane substitué en N.
EMI2.3
La préparation de 1. 3-1Icïroxyal,T? :ai:¯e, qui été peu décrite à ce jour, se fait par réduction 'es ;;1.-1::':1% p-cétoniques, des dérivés de l'acide cyanacétique, des tildes-esters rn..,1oniqu,,;s, et par transforn-tiou des 3-1;yfiroxjalkylii;logê<mres à l'aide d'ariides, ou par ^1y2.^ti n des hyd=oxj,alk%1< ;1=es.
Le tableau ci-aprés indique une série de combinaisons qui ont été préparées par le procédé décrit.
EMI2.4
Exemple R1 R2 R3 R Eb.(mm) Pf n25 rende- 1 2 3 4 ment 1 H C2H5 c2H5 H llz ( 0, 3 j 64-67 - 62% 2 H c 2il5 C3H5 H 129-30 (1) 440 - 71;; 3 H c 2 H 5 c 2 Il 5 C'rI3 I-:4. ( 0s 3 ) - 1,456 60,.
CH C l' C :l 9¯-onn , 455 CH3 ......, 1,.- ^::5 C2::5 (o,Go8-o -L .1.,455 5 5 (0,008-0 1) 5 H CH, u C,H, 4 ;) C3HF 126-130 (0,1) - 1,45 6 6 CH3 C2H5 C2H, CbhS 127-?30 (c,1) - 1,521 50/
Eb (mm) étnt la teupérature d'ébullition sous le vide indiqué exprimé en millimètres de nercure.
Pf étant la température de fusion.
EXEMPLE.
EMI2.5
On dissout 26,2 g de , z-dit?.yl-3-i.; aroxyl,ropylamine et 20,2 g de tri,}tilyl:.;.ine dans 100 c..13 de be:izol rdydre.
<Desc/Clms Page number 3>
EMI3.1
On verse goutte à Eoutte 21,6 g de c:.2oroformiate d'éthyle tout en brassant et en refroidissait, ensuite on chauffe pendant deux heures et deraie à reflux. Apres refroidissement, on aspire le chlorure de trié et l'un élimine le benzol par distillation. On fr&ctionne le résidu. La partie principale passe à 112 C sous un vide de 0,3 mm. La substance se solidifie au refroidisse-
EMI3.2
ment. Après recristai,lisation dans de l'éther de pétrole, elle a une température de fusion use Ô4-67"0.
Rendement : 25 g d'uréthane TI-( 2, 2-diéthyl-3-hydro- xypropyle), c'est-à-dire 62 le la quantité théorique.
EMI3.3
-U0 '----.. .
La présente invention ,. p(ur objet . 1 ) Un procède ,le des esters c*!rbaiai- ques ou substitués en N et ayant pour formule générale
EMI3.4
EMI3.5
dans laquelle à 1 et l.4 sont de l'hydrogène ou des radicaux aD:ye5, aryles ou aralkyles et a2 et :3 sont des radicaux alkyles, aryles ou l'alkyle:;;, ce procédé étant c:#' ctériaé en ce que l'on transforcie la 3-hydroxyalkylsaine correspondante par le chloroformiate d'éthyle.
**ATTENTION** fin du champ DESC peut contenir debut de CLMS **.
<Desc / Clms Page number 1>
EMI1.1
"Proceeds from the preparation of; = rirs of substituted carbamic acid
EMI1.2
killed in N ".
EMI1.3
The ',';., '.': "J ..L1 ;;; C :: 'U": crua.ùlCLiB 01: urethsnes which o..t pf) ur formula,: - = ra7¯e
EMI1.4
EMI1.5
in which R1 and R represent hydrogen or radicals: alkyls, aryls or pralkyls, and Rp and R3 alkyl radicals,
EMI1.6
aryls or aralkyls, are chemicals not yet de-
EMI1.7
writings. The COI: 1.Josés of this cjrje e p # sed, next to a f: .ible toxicity cited in the pi: ar: nacola7iqae test, significant effects on the
<Desc / Clms Page number 2>
central nervous system. For some of these compounds, the sedative activity is particularly :: arched.
EMI2.1
The preparation of the aforementioned urethane :-( 3 = hydroxy-, z disubstituted propyl) is carried out by reacting the corresponding 3-h;, rdroxyalkylamine with ethyl <; loroiornate.
The transformation takes place in an indifferent sc.lvpnt (eg benzol, toluol) in the presence of a hydrochloric acid acceptor.
EMI2.2
(eg triethylsmine, pyridine, dinethyl & ni-1-i-ne). Triethylamine has been found to be the most suitable hydrochloric acid acceptor, because well crystallized chloride can be removed from the reaction mixture without difficulty. After having separated the solvent, the N-substituted urethane is obtained by distillation.
EMI2.3
The preparation of 1. 3-1Icidroxyal, T? : ai: ¯e, which has been little described to date, is done by reduction 'es ;; 1.-1 ::': 1% p-ketones, cyanacetic acid derivatives, rn tildes-esters. ., 1oniqu ,,; s, and by transforn-tiou des 3-1; yfiroxjalkylii; logê <mres using ariides, or by ^ 1y2. ^ Ti n of hyd = oxj, alk% 1 <; 1 = es.
The table below indicates a series of combinations which were prepared by the method described.
EMI2.4
Example R1 R2 R3 R Eb. (Mm) Pf n25 rende- 1 2 3 4 ment 1 H C2H5 c2H5 H llz (0, 3 j 64-67 - 62% 2 H c 2il5 C3H5 H 129-30 (1) 440 - 71 ;; 3 H c 2 H 5 c 2 Il 5 C'rI3 I-: 4. (0s 3) - 1.456 60 ,.
CH C l 'C: l 9¯-onn, 455 CH3 ......, 1, .- ^ :: 5 C2 :: 5 (o, Go8-o -L .1., 455 5 5 (0.008 -0 1) 5 H CH, u C, H, 4;) C3HF 126-130 (0.1) - 1.45 6 6 CH3 C2H5 C2H, CbhS 127-? 30 (c, 1) - 1.521 50 /
Eb (mm) is the boiling temperature under the vacuum indicated expressed in millimeters of mercury.
Pf being the melting temperature.
EXAMPLE.
EMI2.5
26.2 g of, z-dit? .Yl-3-i .; aroxyl, ropylamine and 20.2 g of tri,} tilyl:.;. ine in 100 c..13 of be: izol rdydre.
<Desc / Clms Page number 3>
EMI3.1
21.6 g of ethyl c: .2oroformate are poured in dropwise while stirring and cooling, then the mixture is heated for two hours and under reflux. After cooling, the sorted chloride is sucked off and the benzol is removed by distillation. The residue is fractionated. The main part goes to 112 C under a vacuum of 0.3 mm. The substance solidifies on cooling
EMI3.2
is lying. After recrystallization from petroleum ether, it has a melting point of Ô4-67 "0.
Yield: 25 g of TI- (2, 2-diethyl-3-hydro-xypropyl) urethane, i.e. 62% the theoretical amount.
EMI3.3
-U0 '---- ...
The present invention,. p (ur object. 1) A process, the esters of c *! rbaiaic or substituted in N and having the general formula
EMI3.4
EMI3.5
in which to 1 and 1.4 are hydrogen or aD: ye5, aryl or aralkyl radicals and a2 and: 3 are alkyl, aryl or alkyl radicals: ;;, this process being c: # 'cteriae in that the corresponding 3-hydroxyalkylsaine is transforged with ethyl chloroformate.
** ATTENTION ** end of DESC field can contain start of CLMS **.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE606096A true BE606096A (en) |
Family
ID=192854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE606096D BE606096A (en) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE606096A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1199254B (en) * | 1963-09-20 | 1965-08-26 | Krewel Leuffen Gmbh | Process for the preparation of O, N-dicarbaethoxy derivatives of substituted 1,3-amino alcohols |
| DE1284416B (en) * | 1965-08-04 | 1968-12-05 | Krewel Werke Gmbh | N-AEthyl-N- [2,2-diaethyl-3-diaethylcarbamoyloxy-butyl- (1)] - N ', N'-diaethyl-urea and process for its preparation |
-
0
- BE BE606096D patent/BE606096A/fr unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1199254B (en) * | 1963-09-20 | 1965-08-26 | Krewel Leuffen Gmbh | Process for the preparation of O, N-dicarbaethoxy derivatives of substituted 1,3-amino alcohols |
| DE1284416B (en) * | 1965-08-04 | 1968-12-05 | Krewel Werke Gmbh | N-AEthyl-N- [2,2-diaethyl-3-diaethylcarbamoyloxy-butyl- (1)] - N ', N'-diaethyl-urea and process for its preparation |
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