CS277360B6

CS277360B6 - A method for preparing N- (2,6-difluorobenzoyl) -N'- (4-chlorophenyl) urea

Info

Publication number: CS277360B6
Application number: CS906699A
Authority: CS
Inventors: Peter Rndr Csc Kutschy; Vlastimir Rndr Ficeri; Milan Doc Rndr Csc Dzurilla; Dusan Rndr Csc Koscik
Original assignee: Univerzita P J Safarika
Priority date: 1990-12-27
Filing date: 1990-12-27
Publication date: 1993-01-13
Also published as: CS669990A3

Abstract

Riešenie sa týká nového spósobu pripravy N- (2,6-difluórbenzoyl)-N’-(4-chlórfenyl)močoviny -látky, ktorá vykazuje výraznú insekticídnu účinnosť.N-(2,6-difluórbenzoyl)-N’-(4-chlórfenyl) močovina vzorca I sa připravuje reakciou Salylesteru-N-(2,6-difluórbenzoyl)monotiokarbá movej kyseliny vzorca Π so 4-chlóranilínom vzorca III v benzéne za refluxu v přítomnosti trietylamínu.The solution concerns a new method of preparing N-(2,6-difluorobenzoyl)-N'-(4-chlorophenyl)urea - a substance that exhibits significant insecticidal activity. N-(2,6-difluorobenzoyl)-N'-(4-chlorophenyl)urea of the formula I is prepared by reacting Salylester-N-(2,6-difluorobenzoyl)monothiocarbamic acid of the formula Π with 4-chloroaniline of formula III in refluxing benzene in the presence of triethylamine.

Description

Význam tejto látky spočívá v jej výraznéj insekticídnej účinnosti (Baggiolini M.: Rev. Suisse Vitic. Arboric. Hortic. 11, 15 (1979)). Podlá literatúry sa připravuje reakciou 2,6-difluórbenzoylizokyanátu so 4-chlóranilínom (Aoki I., Okada Y. , Nagase H. , Sato Y.: Jap. pat. 60 246 359 (1985); Chem. Abstr. 105, 24073p (1986)) reakciou 2,6-difluórbenzamidu so 4-chlórfenylkarbamoylchloridom (Gamero B.A.: Špan. pat. 534 727 (1986); Chem. Abstr. 106, P 32623d (1987), metylesteru 4-chlórefenylkarbámovej kyseliny s 2,6-difluórbenzamidom (Oral O., Jose V., Perez E., Luis E.: Špan. pat. 542 417 (1985); Chem. Abstr. 106, P 181154V (1987)), alebo reakciou 2,6-difluórbenzoylchloridu so 4-chlór-fenylmočovinou (Bitter J., Karpati-Adam E., Pfheigel T.: NSR pat. 3 039 069 (1981); Chem. Abstr. 95, P 115093m (1981)).The significance of this substance lies in its marked insecticidal activity (Baggiolini M .: Rev. Suisse Vitic. Arboric. Hortic. 11, 15 (1979)). According to the literature, it is prepared by reacting 2,6-difluorobenzoyl isocyanate with 4-chloroaniline (Aoki I., Okada Y., Nagase H., Sato Y .: Jap. Pat. 60 246 359 (1985); Chem. Abstr. 105, 24073p ( 1986)) by reacting 2,6-difluorobenzamide with 4-chlorophenylcarbamoyl chloride (Gamero BA: Spanish Pat. No. 534,727 (1986); Chem. Abstr. 106, P 32623d (1987)), 4-chlorophenylcarbamic acid methyl ester with 2,6-difluorobenzamide (Oral O., Jose V., Perez E., Luis E .: Spanish Pat. No. 542,417 (1985); Chem. Abstr. 106, P 181154V (1987)), or by reacting 2,6-difluorobenzoyl chloride with 4- chlorophenylurea (Bitter J., Karpati-Adam E., Pfheigel T .: NSR Pat. 3,039,069 (1981); Chem. Abstr. 95, P 115093m (1981)).

Uvedené technologie přípravy však vyžadujú pracovat so zdraviu škodlivými toxickými látkami.However, these preparation technologies require working with toxic substances that are harmful to health.

Túto nevýhodu v podstatnéj miere odstraňuje spósob podlá vynálezu, ktorého podstata spočívá v tom, že na S-alylester-N-(2,6-difluórbenzoyl) monotiokarbámovú kyselinu vzorca IIThis disadvantage is substantially eliminated by the process according to the invention, which consists in the fact that S-allyl ester-N- (2,6-difluorobenzoyl) monothiocarbamic acid of the formula II

(II) sa pósobí 4-chlóranilínom vzorca III(II) is treated with 4-chloroaniline of formula III

(III) v benzéne za refluxu v přítomnosti trietylamínu.(III) in benzene at reflux in the presence of triethylamine.

Výhodou spósobu přípravy N-(2,6-difluórbenzoyl)-Ν'-(4-chlórfenyl) močoviny podlá vynálezu je jednoduchý pr^covný postup ako aj to, že produkt sa získá z lahko dostupných, stabilizovaných a zdraviu neškodných východiskových látok v dobrom výtažku a čistotě.The advantage of the process for the preparation of N- (2,6-difluorobenzoyl) -N '- (4-chlorophenyl) urea according to the invention is the simple working procedure as well as that the product is obtained from readily available, stabilized and harmless starting materials in good extract and purity.

Příklad 1Example 1

Za laboratórnej teploty sa v 15 ml benzénu rozpustí 2 g (8 mmol) S-alylesteru-N-(2,6-difluórbenzoyl)monotiokarbámovej ky seliny, 1 g (8 mmol) 4-chlóranilínu a 0,08 g (0,11 ml; 0,8 mmol) trietylaminu. Potom sa reakčná zmes réfluxuje 5 min. Vylúčená zrazenina produktu sa po ochladení na laboratórnu teplotu odsaje, vysuší a kryštalizuje z benzenu. Výťažok 1,68 g (70 %), t.t. 232 až 233 °C. Pre C₁₄H_gClF₂N₂O₂ (310,7) vypočítané: 54,12 % C;At room temperature, 2 g (8 mmol) of N- (2,6-difluorobenzoyl) monothiocarbamic acid S-allyl ester, 1 g (8 mmol) of 4-chloroaniline and 0.08 g (0.11 g) were dissolved in 15 ml of benzene. ml; 0.8 mmol) triethylamine. The reaction mixture is then refluxed for 5 minutes. After cooling to room temperature, the precipitate formed is filtered off with suction, dried and crystallized from benzene. Yield 1.68 g (70%), mp 232-233 ° C. For C ₁₄ H _g ClF ₂ N ₂ O ₂ (310.7) calculated: 54.12% C;

2,92 % H; 9,02 % N; zistené: 54,29 % C; 2,81 % H; 9,17 % N.IČ (chloroform):ý(CO-NH-CO) 1690-a 1716 cm“¹.2.92% H; 9.02% N; found: 54.29% C; 2.81% H; 9.17% N.IČ (chloroform): γ (CO-NH-CO) 1690-a 1716 cm- ¹ .

Claims

PATENT EQUIPMENT OK

Process for the preparation of N- (2,6-difluorobenzoyl) -N '- (4-chlorophenyl) urea of formula I ·

characterized in that the S-allyl ester of N- (2,6-difluorobenzoyl) monothiocarbamic acid of formula II

is treated with 4-chloroaniline of formula III

in benzene at reflux in the presence of triethylamine.