CH399433A - Process for the preparation of carbamic acid esters of substituted benzyl alcohols - Google Patents
Process for the preparation of carbamic acid esters of substituted benzyl alcoholsInfo
- Publication number
- CH399433A CH399433A CH1061061A CH1061061A CH399433A CH 399433 A CH399433 A CH 399433A CH 1061061 A CH1061061 A CH 1061061A CH 1061061 A CH1061061 A CH 1061061A CH 399433 A CH399433 A CH 399433A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- benzyl alcohols
- benzyl
- carbamic acid
- acid
- Prior art date
Links
- 235000019445 benzyl alcohol Nutrition 0.000 title claims description 11
- 150000003938 benzyl alcohols Chemical class 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims description 4
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 title claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- -1 chlorocarbonic acid ester Chemical class 0.000 claims description 10
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000005915 ammonolysis reaction Methods 0.000 claims description 2
- 230000001773 anti-convulsant effect Effects 0.000 claims description 2
- 239000001961 anticonvulsive agent Substances 0.000 claims description 2
- 229960003965 antiepileptics Drugs 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- SNGLYCMNDNOLOF-UHFFFAOYSA-N benzyl phenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OCC1=CC=CC=C1 SNGLYCMNDNOLOF-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 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
- 238000001816 cooling Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229940035363 muscle relaxants Drugs 0.000 description 2
- 239000003158 myorelaxant agent Substances 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- XHMKGDUAGDFSHL-UHFFFAOYSA-N (2-butoxyphenyl)methanol Chemical compound CCCCOC1=CC=CC=C1CO XHMKGDUAGDFSHL-UHFFFAOYSA-N 0.000 description 1
- XHTUZBFAOYRMHI-UHFFFAOYSA-N (4-bromophenyl)methyl carbamate Chemical compound NC(=O)OCC1=CC=C(Br)C=C1 XHTUZBFAOYRMHI-UHFFFAOYSA-N 0.000 description 1
- UBOFXBQTRQSKMY-UHFFFAOYSA-N 1-(2-chlorophenyl)propan-1-ol Chemical compound CCC(O)C1=CC=CC=C1Cl UBOFXBQTRQSKMY-UHFFFAOYSA-N 0.000 description 1
- VCZXDPUECVELRF-UHFFFAOYSA-N 1-(2-chlorophenyl)propyl carbamate Chemical compound NC(=O)OC(CC)C1=CC=CC=C1Cl VCZXDPUECVELRF-UHFFFAOYSA-N 0.000 description 1
- LQAPSMWXDFJNGU-UHFFFAOYSA-N 2,2,2-trichloro-1-(4-chlorophenyl)ethanol Chemical compound ClC(Cl)(Cl)C(O)C1=CC=C(Cl)C=C1 LQAPSMWXDFJNGU-UHFFFAOYSA-N 0.000 description 1
- FSMCOBJDZVRWIZ-UHFFFAOYSA-N 2-butoxybenzaldehyde Chemical compound CCCCOC1=CC=CC=C1C=O FSMCOBJDZVRWIZ-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 206010021118 Hypotonia Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- OFSLZWKZFLERLT-UHFFFAOYSA-N NC(OC(C(Cl)(Cl)Cl)C(C=C1)=CC=C1Cl)=O Chemical compound NC(OC(C(Cl)(Cl)Cl)C(C=C1)=CC=C1Cl)=O OFSLZWKZFLERLT-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- QHDUJTCUPWHNPK-UHFFFAOYSA-N methyl 7-methoxy-2h-indazole-3-carboxylate Chemical compound COC1=CC=CC2=C(C(=O)OC)NN=C21 QHDUJTCUPWHNPK-UHFFFAOYSA-N 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- VEDDBHYQWFOITD-UHFFFAOYSA-N para-bromobenzyl alcohol Chemical compound OCC1=CC=C(Br)C=C1 VEDDBHYQWFOITD-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Carbaminsäureestern substituierter Benzylalkohole
Gegenstand der Erfindung ist ein Verfahren zur Herstellung therapeutisch wirksamer Benzylcarbamate der Formel
EMI1.1
in der R ein Wasserstoffatom oder eine unsubstituierte oder durch mindestens 1 Chloratom substituierte, gegebenenfalls verzweigte Alkylgruppe darstellt und in der X ein Halogenatom oder eine Alkoxygruppe bedeutet, dadurch gekennzeichnet, dass man entweder a) die entsprechenden Benzylalkohole zunächst mit Phosgen und den so erhaltenen Chlorkohlensäureester mit Ammoniak umsetzt oder dass man b) diese Benzylalkohole mit reaktionsfähigen Derivaten der Carbaminsäure umgesetzt oder dass man c) diese Benzylalkohole zunächst mit einem Phenolester der Chlorameisensäure zur Reaktion bringt,
worauf der so erhaltene O-Benzyl-O'-phenylkohlensäureester durch Ammonolyse in das entsprechende Benzylcarbamat übergeführt wird, oder dass man d) die Benzylalkohole mit Alkalicyanaten in Gegenwart inerter Lösungsmittel, wie z. B. Chloroform oder Methylenchlorid, und einer Säure, z. B. einer in a-Stellung chlorierten niederen Fettsäure, zur Reaktion bringt.
Die neuen Verbindungen der Erfindung üben eine antikonvulsive, tranquilisierende und vor allem muskelrelaxierende Wirkung aus. tSberraschender- weise hält die Muskelrelaxation bei diesen Verbindungen viel besser an als bei bekannten Muskelrelaxantien. Die extrem lange Wirkungsdauer tritt selbst bei peroraler Verabreichung in Erscheinung.
So ruft z. B. die Verbindung der Formel II (Beispiel 2)
EMI1.2
im Versuch am Schräggitter-Test für Muskelrelaxan- tien und sedative Wirkung, vergleiche J. Pharm. Exp.
Therap. 100, 333 (1950) und 122, 517 (1958), bei peroraler Verabreichung in einer Dosis von 400 mg/kg an Mäusen bei 50 % der eingesetzten Tiere einen etwa 8 Stunden anhaltenden Rutscheffekt hervor, während sich die bekannte Verbindung
EMI1.3
im Vergleichsversuch als praktisch wirkungslos erwies.
Die Verbindungen der Formel I werden erfindungsgemäss vorzugsweise in der Weise hergestellt, dass man die entsprechenden Carbinole, z. B. in bekannter Weise, mit Cyansäure, Harnstoffchlorid, Harnstoff (eventuell unter Zusatz von Schwermetallsalzen) oder Harnstoffsalzen (z.B. Harnstoffnitrat) umgesetzt oder mit Urethan (nötigenfalls unter Zusatz von Katalysatoren) oder Phosgen (eventuell unter Zusatz einer tertiären Base) und Ammoniak.
Beispiel 1 p-Brombenzyl-carbamat
EMI1.4
p-Brombenzylalkohol wurde in einem 10% eigen Überschuss einer 20% eigen Lösung von Phosgen in Toluol gelöst. Nach beendigter HCl-Abspaltung wurde der Phosgenüberschuss mit trockener Luft verdrängt und die Toluollösung unter Eiskühlung zum gleichen Volumen 25 % igen Ammoniaks getropft, worauf das Carbamat in Blättern auskristallisierte.
Nach wiederholter Umkristallisation betrug der Schmelzpunkt 150-1520.
Berechnet: C 41,7 H 3,5%
Gefunden: C 41,9 H 3,6%
Beispiel 2 o-Chlorphenyl-äthyl-carbinol-carbamat
EMI2.1
Zu einer Lösung von 1 Teil o-Chlorphenyl-äthyl- carbinol in 10 Teilen Äther fügte man 5-10% mehr als die theoretische Menge Carbaminsäurechlorid (NH2COC1) und liess 1 Tag stehen. Die Ätherlösung wurde sodann mit Eiswasser gewaschen, abgetrennt, getrocknet, eingedampft und der Rückstand mit Leichtbenzin verrieben, worauf er kristallisierte. Nach der Umkristallisation betrug der Schmelzpunkt 108 bis 1090.
Berechnet: Cl 16,6%; Gefunden: 16,8%
Beispiel 3 p-Chlorphenyl-trichlormethyl-carbinol-carbamat
EMI2.2
21,5 Teile p-Chlorphenyl-trichlormethyl-carbinol wurden in 41 Teilen Toluol gelöst, 6,54 Teile Pyridin zugefügt und diese Mischung unter Eiskühlung zu 41 Teilen einer 20% eigen Phosgenlösung in Toluol getropft. Man rührte nach Zusatz von 50 Teilen Toluol 8 Stunden bei Raumtemperatur, tropfte rasch unter Eiskühlung 200 Teile 34 % igen Ammoniak zu, rührte 15 Stunden, trennte die organische Phase ab, trocknete sie und entfernte das Toluol im Vakuum.
Aus dem Rückstand wurde durch Umkristallisation aus Benzol das Carbamat vom Schmelzpunkt 187 bis 1880 erhalten. Ber. N 4,6; Gef. 4,5%.
Nach dem oben beschriebenen Verfahren wurden folgende weitere Carbamate hergestellt:
EMI2.3
<tb> Name <SEP> Formel <SEP> Smp. <SEP> Analyt. <SEP> Daten
<tb> p-Chlorbenzyl- <SEP> C1-C <SEP> -CH200CNH2 <SEP> 1400 <SEP> Ber. <SEP> N <SEP> 7,55
<tb> carbamat <SEP> Cl-\-7-CH2OOCNH2 <SEP> Gef. <SEP> 7,75 <SEP> %
<tb> p-Chlorphenyl-äthyl <SEP> C1CH-C2H5 <SEP> 68-690 <SEP> Ber. <SEP> C1 <SEP> 16,65 <SEP> %
<tb> carbinolcarbamat <SEP> OOCNH2 <SEP> Gef. <SEP> C1 <SEP> 16,65%
<tb> o-Chlorphenylpropyl- <SEP> Cl <SEP> 450 <SEP> Ber. <SEP> 0 <SEP> 57,9; <SEP> H <SEP> 6,2;
<tb> carbinolcarbamat <SEP> 1 <SEP> 450 <SEP> HCHCH <SEP> Gef. <SEP> Cl <SEP> 15,6%
<tb> <SEP> -CH-C <SEP> Gef. <SEP> C <SEP> 57,8;
<SEP> H <SEP> 6,2;
<tb> <SEP> OOCNH2 <SEP> C1 <SEP> 15,5%
<tb>
Beispiel 4 o-Butoxybenzylcarbamat
EMI2.4
Zu 18 g o-Butoxybenzylalkohol (hergestellt z. B. durch Hydrierung von o-Butoxybenzaldehyd mit Kupferchromit bei 1400 und einem Druck von 165 Atmosphären; Siedepunkt 1180/3 mm Hg, nu22.60 = 1,5160) in 180 cms Ather fügt man bei 0 8,8 g NH2COC1 zu, lässt 2 Tage bei 200 stehen und arbeitet wie in den vorhergehenden Beispielen auf. Nach der Umkristallisation aus Cyclohexan erhält man 17,8 g nadelförmiges Produkt vom Schmelzpunkt 88-89,50.
Berechnet: C 64,7 H 7,7 N 6,3 %
Gefunden: C 64,5 H 7,7 N 6,3 %
Process for the preparation of carbamic acid esters of substituted benzyl alcohols
The invention relates to a process for the preparation of therapeutically active benzyl carbamates of the formula
EMI1.1
in which R is a hydrogen atom or an unsubstituted or substituted by at least 1 chlorine atom, optionally branched alkyl group and in which X is a halogen atom or an alkoxy group, characterized in that either a) the corresponding benzyl alcohols are initially mixed with phosgene and the chlorocarbonic acid ester thus obtained with Ammonia is converted or that b) these benzyl alcohols are reacted with reactive derivatives of carbamic acid or that c) these benzyl alcohols are first reacted with a phenol ester of chloroformic acid,
whereupon the O-benzyl-O'-phenyl carbonate obtained in this way is converted into the corresponding benzyl carbamate by ammonolysis, or that d) the benzyl alcohols with alkali metal cyanates in the presence of inert solvents, such as. B. chloroform or methylene chloride, and an acid, e.g. B. a chlorinated in a-position lower fatty acid reacts.
The new compounds of the invention exert an anticonvulsant, tranquilizing and, above all, muscle-relaxing effect. Surprisingly, muscle relaxation persists much better with these compounds than with known muscle relaxants. The extremely long duration of action is evident even with oral administration.
So calls z. B. the compound of formula II (Example 2)
EMI1.2
in the experiment on the inclined grid test for muscle relaxants and sedative effects, compare J. Pharm. Exp.
Therap. 100, 333 (1950) and 122, 517 (1958), when administered orally at a dose of 400 mg / kg to mice, 50% of the animals used produced a sliding effect lasting about 8 hours, while the known compound
EMI1.3
proved to be practically ineffective in the comparative experiment.
According to the invention, the compounds of formula I are preferably prepared in such a way that the corresponding carbinols, eg. B. in a known manner, with cyanic acid, urea chloride, urea (possibly with the addition of heavy metal salts) or urea salts (e.g. urea nitrate) or with urethane (if necessary with the addition of catalysts) or phosgene (possibly with the addition of a tertiary base) and ammonia.
Example 1 p-bromobenzyl carbamate
EMI1.4
p-Bromobenzyl alcohol was dissolved in a 10% own excess of a 20% own solution of phosgene in toluene. After the elimination of HCl had ended, the excess phosgene was displaced with dry air and the toluene solution was added dropwise to the same volume of 25% ammonia while cooling with ice, whereupon the carbamate crystallized in leaves.
After repeated recrystallization, the melting point was 150-1520.
Calculated: C 41.7 H 3.5%
Found: C 41.9 H 3.6%
Example 2 o-chlorophenyl-ethyl-carbinol-carbamate
EMI2.1
To a solution of 1 part of o-chlorophenyl-ethyl-carbinol in 10 parts of ether, 5-10% more than the theoretical amount of carbamic acid chloride (NH2COC1) was added and left to stand for 1 day. The ether solution was then washed with ice water, separated off, dried, evaporated and the residue triturated with light gasoline, whereupon it crystallized. After recrystallization, the melting point was 108-1090.
Calculated: Cl 16.6%; Found: 16.8%
Example 3 p-Chlorophenyl trichloromethyl carbinol carbamate
EMI2.2
21.5 parts of p-chlorophenyl-trichloromethyl-carbinol were dissolved in 41 parts of toluene, 6.54 parts of pyridine were added and this mixture was added dropwise to 41 parts of a 20% own phosgene solution in toluene while cooling with ice. After addition of 50 parts of toluene, the mixture was stirred for 8 hours at room temperature, 200 parts of 34% ammonia were quickly added dropwise with ice-cooling, the mixture was stirred for 15 hours, the organic phase was separated off and dried and the toluene was removed in vacuo.
The carbamate with a melting point of 187-1880 was obtained from the residue by recrystallization from benzene. Ber. N 4.6; Found 4.5%.
The following additional carbamates were produced using the method described above:
EMI2.3
<tb> Name <SEP> Formula <SEP> Smp. <SEP> Analyt. <SEP> data
<tb> p-chlorobenzyl- <SEP> C1-C <SEP> -CH200CNH2 <SEP> 1400 <SEP> calc. <SEP> N <SEP> 7.55
<tb> carbamate <SEP> Cl - \ - 7-CH2OOCNH2 <SEP> found <SEP> 7.75 <SEP>%
<tb> p-chlorophenyl-ethyl <SEP> C1CH-C2H5 <SEP> 68-690 <SEP> Ber. <SEP> C1 <SEP> 16.65 <SEP>%
<tb> carbinol carbamate <SEP> OOCNH2 <SEP> found <SEP> C1 <SEP> 16.65%
<tb> o-Chlorophenylpropyl- <SEP> Cl <SEP> 450 <SEP> Ber. <SEP> 0 <SEP> 57.9; <SEP> H <SEP> 6.2;
<tb> carbinol carbamate <SEP> 1 <SEP> 450 <SEP> HCHCH <SEP> Gef. <SEP> Cl <SEP> 15.6%
<tb> <SEP> -CH-C <SEP> Found <SEP> C <SEP> 57.8;
<SEP> H <SEP> 6.2;
<tb> <SEP> OOCNH2 <SEP> C1 <SEP> 15.5%
<tb>
Example 4 o-Butoxybenzyl carbamate
EMI2.4
To 18 g of o-butoxybenzyl alcohol (prepared e.g. by hydrogenating o-butoxybenzaldehyde with copper chromite at 1400 and a pressure of 165 atmospheres; boiling point 1180/3 mm Hg, nu22.60 = 1.5160) in 180 cms of ether is added at 0, 8.8 g of NH2COC1 are allowed, left to stand for 2 days at 200 and worked up as in the previous examples. After recrystallization from cyclohexane, 17.8 g of needle-shaped product with a melting point of 88-89.50 are obtained.
Calculated: C 64.7 H 7.7 N 6.3%
Found: C 64.5 H 7.7 N 6.3%
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1061061A CH399433A (en) | 1961-09-13 | 1961-09-13 | Process for the preparation of carbamic acid esters of substituted benzyl alcohols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1061061A CH399433A (en) | 1961-09-13 | 1961-09-13 | Process for the preparation of carbamic acid esters of substituted benzyl alcohols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH399433A true CH399433A (en) | 1965-09-30 |
Family
ID=4365014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1061061A CH399433A (en) | 1961-09-13 | 1961-09-13 | Process for the preparation of carbamic acid esters of substituted benzyl alcohols |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH399433A (en) |
-
1961
- 1961-09-13 CH CH1061061A patent/CH399433A/en unknown
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