CS261045B1 - N- (2,6-dichlorophenyl) -benzimidoyichloride - Google Patents
N- (2,6-dichlorophenyl) -benzimidoyichloride Download PDFInfo
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- CS261045B1 CS261045B1 CS866328A CS632886A CS261045B1 CS 261045 B1 CS261045 B1 CS 261045B1 CS 866328 A CS866328 A CS 866328A CS 632886 A CS632886 A CS 632886A CS 261045 B1 CS261045 B1 CS 261045B1
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- dichlorophenyl
- benzimidoyl chloride
- benzimidoyichloride
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Abstract
Řešení se týká N-(2,6-dichlorfenyl)- -benzimidoylchloridu; tato nová látka slouží jako meziprodukt pro příptavu sodné soli diclofenacu, která je žádaným léčivem s protibolestivým a protizánětlivým účinkem.The solution concerns N-(2,6-dichlorophenyl)-benzimidoyl chloride; this new substance serves as an intermediate for the preparation of diclofenac sodium, which is a desired drug with analgesic and anti-inflammatory effects.
Description
Vynález se týká N-(2,6-dichlorfenyl)-benzimidoylchloridu vzorce IThe invention relates to N- (2,6-dichlorophenyl) -benzimidoyl chloride of formula I
ClCl
ClCl
Cl který je meziproduktem přípravy o-(2,6-dichloranilino)-fenyloctové kyseliny, jejíž sodná sůl (diclofenac natrium) je rozšířeným léčivem s protibolestivým a protizánětlivým účinkem.Cl, which is an intermediate for the preparation of o- (2,6-dichloroanilino) -phenylacetic acid, whose sodium salt (diclofenac sodium) is a widespread drug with an anti-pain and anti-inflammatory effect.
Nová sloučenina vzorce X se připravuje reakcí 2,6-dichloranilidu kyseliny benzoové s chlo ridem fosforečným, případně za přítomnosti aprotického rozpouštědla (toluen, ethylbenzen, xylen, technický benzín, chlorované alifatické nebo aromatické uhlovodíky apod.), v rozmezí teplot 30 °C až 112 °C; po oddestilování oxidochloridu fosforečného a případně přítomného aprotického rozpouštědla se N-(2,6-dichlorfenyl)-benzimidoylchlorid izoluje vakuovou destilací Získá se slabě nažloutlý viskózní olej, který stáním zkrystaluje; připravený N-(2,6-dichlor-. fenyl)-benzimidoylchlorid je 98,5% (stanoveno spektrálně a plynovou chromatografií) a vykazuje t.t. 51 °C až 52 °C a t.v. 200 °C až 203 °C při tlaku 1,2 kPa.The novel compound of formula X is prepared by reacting 2,6-dichloroanilide benzoic acid with phosphorus pentachloride, optionally in the presence of an aprotic solvent (toluene, ethylbenzene, xylene, industrial gasoline, chlorinated aliphatic or aromatic hydrocarbons, etc.), in the temperature range of 30 ° C to 112 [deg.] C .; after distilling off the phosphorus pentoxide and the possibly present aprotic solvent, N- (2,6-dichlorophenyl) -benzimidoyl chloride is isolated by vacuum distillation to give a slightly yellow viscous oil which crystallizes on standing; prepared N- (2,6-dichloro-phenyl) -benzimidoyl chloride was 98.5% (determined by spectral and gas chromatography) and showed m.p. 51 ° C to 52 ° C; 200 ° C to 203 ° C at a pressure of 1.2 kPa.
Následující příklad přípravy sloučeniny podle vynálezu látky pouze dokládá ale neomezuje.The following example of the preparation of the compound of the invention illustrates, but does not limit, the substances.
PříkladExample
Směs 26,6 g (0,10 mol) 2,6-dichloranilidu kyseliny benzoové, 21,0 g (0,10 mol) chloridu fosforečného a 10 ml oxidochloridu fosforečného se za stálého míchání zahřívá na vodní lázni; po proběhnutí úvodní exothermní reakce se zhomogenizovaná reakční směs zahřívá 3 h na teplotu 90 °C až 95 °C. Nasazený i reakcí vzniklý oxidochlorid fosforečný se z míchané reakční směsi oddestiluje za vakua vodní vývěvy, vzniklý N-(2,6-dichlorfenyl)-benzimidoylchlorid se izoluje destilací za vakua olejové vývěvy při teplotě 200 °C až 203 °C a tlaku 1,2 kPa; vakuovou destilací se získá 26,5 g (tj. 93,0 % th.) slabě nažloutlého olejovitého produktu, který stáním krystalicky ztuhne. Získaný N-(2,6-dichlorfenyl)-benzimidoylchlorid je podle analytických stanovení 98,5% a vykazuje' t.t. 51 °C až 52 °C.A mixture of 26.6 g (0.10 mol) of benzoic acid 2,6-dichloroanilide, 21.0 g (0.10 mol) of phosphorus pentachloride and 10 ml of phosphorus oxychloride is heated on a water bath while stirring; after the initial exothermic reaction is completed, the homogenized reaction mixture is heated at 90 ° C to 95 ° C for 3 hours. The resulting phosphorus pentoxide (II) formed in the reaction mixture is distilled off from the stirred reaction mixture under a water pump vacuum. The resulting N- (2,6-dichlorophenyl) -benzimidoyl chloride is isolated by distillation under an oil pump vacuum at 200 ° C to 203 ° C and 1.2. kPa; vacuum distillation yielded 26.5 g (i.e. 93.0% th.) of a slightly yellowish oily product which solidified on standing. The N- (2,6-dichlorophenyl) -benzimidoyl chloride obtained was 98.5% by analytical analysis and showed a m.p. 51 ° C to 52 ° C.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS866328A CS261045B1 (en) | 1986-09-01 | 1986-09-01 | N- (2,6-dichlorophenyl) -benzimidoyichloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS866328A CS261045B1 (en) | 1986-09-01 | 1986-09-01 | N- (2,6-dichlorophenyl) -benzimidoyichloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS632886A1 CS632886A1 (en) | 1988-06-15 |
| CS261045B1 true CS261045B1 (en) | 1989-01-12 |
Family
ID=5410066
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS866328A CS261045B1 (en) | 1986-09-01 | 1986-09-01 | N- (2,6-dichlorophenyl) -benzimidoyichloride |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS261045B1 (en) |
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1986
- 1986-09-01 CS CS866328A patent/CS261045B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS632886A1 (en) | 1988-06-15 |
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