DE1229513B - Process for making fluorinated urethanes - Google Patents

Process for making fluorinated urethanes

Info

Publication number
DE1229513B
DE1229513B DEN20374A DEN0020374A DE1229513B DE 1229513 B DE1229513 B DE 1229513B DE N20374 A DEN20374 A DE N20374A DE N0020374 A DEN0020374 A DE N0020374A DE 1229513 B DE1229513 B DE 1229513B
Authority
DE
Germany
Prior art keywords
fluorinated urethanes
general formula
making fluorinated
pentafluorophenol
pyridine
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
Application number
DEN20374A
Other languages
German (de)
Inventor
Leon Jerzy Belf
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
National Smelting Co Ltd
Original Assignee
National Smelting Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by National Smelting Co Ltd filed Critical National Smelting Co Ltd
Publication of DE1229513B publication Critical patent/DE1229513B/en
Pending legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
    • 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)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Emergency Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

AUSLEGESCHRIFTEDITORIAL

Int. α.:Int. α .:

C07cC07c

Deutsche Kl.: 12 ο-17/01 German class: 12 ο -17/01

Nummer: 1229 513Number: 1229 513

Aktenzeichen: N 20374IV b/12 οFile number: N 20374IV b / 12 ο

Anmeldetag: 25. Juli 1961 Filing date: July 25, 1961

Auslegetag: !.Dezember 1966Opening day:! December 1966

Die Erfindung betrifft ein Verfahren zur Herstellung fluorierter Urethane der allgemeinen FormelThe invention relates to a process for the production of fluorinated urethanes of the general formula

(R)2-N-COOC6F5 (R) 2 -N-COOC 6 F 5

wobei R eine Phenyl- oder niedermolekulare Alkylgruppe bedeutet, welches dadurch gekennzeichnet ist, daß ein Säurechlorid der allgemeinen Formelwhere R is a phenyl or low molecular weight alkyl group, which is characterized by is that an acid chloride of the general formula

(R)2 — NCOCl(R) 2 - NCOCl

wobei R die obengenannte Bedeutung hat, mit Pentafluorphenol in Gegenwart von Pyridin bei erhöhter Temperatur umgesetzt wird. Die nach der Erfindung hergestellten Verbindungen sind Sedativa und Hypnotika und zeigen günstige Wirkung bei bestimmten Leukämiearten.where R has the abovementioned meaning with pentafluorophenol is reacted in the presence of pyridine at elevated temperature. According to the invention Compounds produced are sedatives and hypnotics and show beneficial effects on certain Types of leukemia.

Umsetzungen von Verbindungen, die die C6F5-Gruppe aufweisen, sind noch wenig durchforscht, und es war daher nicht ohne weiteres zu erwarten, daß bei dem erfindungsgemäßen Verfahren, welches auch von Verbindungen ausgeht, bei denen der Perfluorphenylrest direkt mit einer funktionellen Gruppe verknüpft ist, ein einwandfreier Ablauf der Umsetzung eintreten würde.Conversions of compounds which have the C 6 F 5 group have not yet been thoroughly researched, and it was therefore not immediately to be expected that in the process according to the invention, which also starts from compounds in which the perfluorophenyl radical is directly linked to a functional group is linked, the implementation would go smoothly.

Die Erfindung wird im folgenden an Hand der Ausführungsbeispiele erläutert:The invention is explained below using the exemplary embodiments:

Beispiel 1example 1

18,4 g (0,1 Mol) Pentafluorphenol und 25,5 g (10% Überschuß) N - (Diphenyl) - carbamylchlorid werden in Gegenwart von 30 ml Pyridin unter Rückfluß gekocht. Bei dem Verdünnen mit Wasser wird N-(Diphenyl)-pentafluorphenylurethan ausgefällt, das nach dem Umkristallisieren aus Tetrachlorkohlenstoff oder Äthylalkohol einen F. = 112 bis 113 0C zeigt. Die Ausbeute beträgt 22,8 g, entsprechend 60 % der Theorie.18.4 g (0.1 mol) of pentafluorophenol and 25.5 g (10% excess) of N - (diphenyl) - carbamyl chloride are refluxed in the presence of 30 ml of pyridine. In the dilution with water, N- (diphenyl) -pentafluorphenylurethan is precipitated, which shows a F. after recrystallization from carbon tetrachloride or ethyl alcohol = 112-113 0 C. The yield is 22.8 g, corresponding to 60% of theory.

Analyse für C19H10F5NO2:
Gefunden ... C 60,4%, H 2,9 %, F 23,2 %; berechnet ... C 60,2%, H 2,65%, F 25,0%.Analysis for C 19 H 10 F 5 NO 2 :
Found ... C 60.4%, H 2.9%, F 23.2%; calculated ... C 60.2%, H 2.65%, F 25.0%.

B e i s ρ i e 1 2B e i s ρ i e 1 2

9,6 g (0,05MoI; Reinheit 96%) Pentafluorphenol und 7,5 g (12% Überschuß) N-(Diäthyl)-carbamylchlorid werden in 25 ml Pyridin unter Rückfluß erhitzt. Nach 2stündigem Kochen wird das Umsetzungsgemisch in Wasser gegossen. Die abgetrennte organische Schicht ergibt zusammen mit dem ätheri-Verfahren zur Herstellung fluorierter Urethane9.6 g (0.05 mol; purity 96%) pentafluorophenol and 7.5 g (12% excess) of N- (diethyl) carbamyl chloride are refluxed in 25 ml of pyridine heated. After boiling for 2 hours, the reaction mixture is poured into water. The severed one organic layer results together with the etheri process for the production of fluorinated urethanes

Anmelder:Applicant:

The National Smelting Company Limited, LondonThe National Smelting Company Limited, London

Vertreter:Representative:

Dipl.-Ing. K. A. Brose, Patentanwalt, Pullach (Isartal), Wiener Str. 2Dipl.-Ing. K. A. Brose, patent attorney, Pullach (Isartal), Wiener Str. 2

Als Erfinder benannt:Named as inventor:

Leon Jerzy BeIf,Leon Jerzy BeIf,

Avonmouth, Bristol (Großbritannien)Avonmouth, Bristol (UK)

Beanspruchte Priorität:
Großbritannien vom 26. Juli 1960 (25 925), vom 12. Juli 1961Claimed priority:
Great Britain, July 26, 1960 (25 925), July 12, 1961

sehen Extrakt der wäßrigen Schicht bei der Destillation N-(Diäthyl)-pentafluorphenylurethan, das einen Kp. 7 = 103 bis 1060C zeigt. Die Ausbeute beträgt 12,5 g, entsprechend 88 % der Theorie.see extract the aqueous layer in the distillation N- (diethyl) -pentafluorphenylurethan showing a Kp. 7 = 103 to 106 0 C. The yield is 12.5 g, corresponding to 88% of theory.

Analyse für C10H10F5NO2:Analysis for C 10 H 10 F 5 NO 2 :

Gefunden ... C 47,1%, H 3,7%, F 32,4%; berechnet ... C 46,8%, H 3,5%, F 33,5%.Found ... C 47.1%, H 3.7%, F 32.4%; calculated ... C 46.8%, H 3.5%, F 33.5%.

Claims (1)

Patentanspruch:Claim: Verfahren zur Herstellung fluorierter Urethane der allgemeinen FormelProcess for the preparation of fluorinated urethanes of the general formula (R)2-N-COOC6F5 (R) 2 -N-COOC 6 F 5 wobei R eine Phenyl- oder niedermolekulare Alkylgruppe bedeutet, dadurch gekennzeichnet, daß ein Säurechlorid der allgemeinen Formelwhere R denotes a phenyl or low molecular weight alkyl group, characterized in that that an acid chloride of the general formula (R)2-NCOCl(R) 2 -NCOCl wobei R die obengenannte Bedeutung hat, mit Pentafluorphenol in Gegenwart von Pyridin bei erhöhter Temperatur umgesetzt wird.where R has the abovementioned meaning, with pentafluorophenol in the presence of pyridine elevated temperature is implemented. In Betracht gezogene Druckschriften: Journal of organic chemistry, Bd. 21 (1956), S. 1036.Papers considered: Journal of organic chemistry, Vol. 21 (1956), p. 1036.
DEN20374A 1960-07-26 1961-07-25 Process for making fluorinated urethanes Pending DE1229513B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1229513X 1960-07-26

Publications (1)

Publication Number Publication Date
DE1229513B true DE1229513B (en) 1966-12-01

Family

ID=10884350

Family Applications (1)

Application Number Title Priority Date Filing Date
DEN20374A Pending DE1229513B (en) 1960-07-26 1961-07-25 Process for making fluorinated urethanes

Country Status (1)

Country Link
DE (1) DE1229513B (en)

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

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