CS259821B1 - Benzoic acid 2,6-dichloroanilide - Google Patents
Benzoic acid 2,6-dichloroanilide Download PDFInfo
- Publication number
- CS259821B1 CS259821B1 CS866329A CS632986A CS259821B1 CS 259821 B1 CS259821 B1 CS 259821B1 CS 866329 A CS866329 A CS 866329A CS 632986 A CS632986 A CS 632986A CS 259821 B1 CS259821 B1 CS 259821B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- dichloroanilide
- benzoic acid
- formula
- water
- preparation
- Prior art date
Links
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Řešeni se týká 2,6-diChloranilldu kyseliny benzoové; tato nová látka slouží jako meziprodukt pro přípravu sodné soli diclofenacu, která je žádaným léčivem s protibolestlvým a protizánětlivým účinkem.The solution concerns 2,6-dichloroanilide of benzoic acid; 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 2,6-dichloranilidu kyseliny benzoové vzorce I
který je meziproduktem přípravy a-(2,6-di-chloranilino)-fenyloctové kyseliny, jejíž sodná sůl (diclofenac natrium] je rozšířeným léčivem s protibolestivým a protizánětlivým účinkem.
Nová sloučenina vzorce I se připravuje reakcí 2,6-dichloranilinu s benzoylchlori-dem za přítomnosti ekvivalentního množství pyridinu nebo terciárního aminu jako pro-tonakceptoru, v rozmezí teplot 20° až 110° Celsia; po zředění reakční směsi vodou se vyloučený surový 2,6-dichloranilid kyseliny benzoové t. t. 147 ° až 149 °C izoluje filtrací. Čistý 2,6-dichloranilid kyseliny benzoové jako bílá krystalická látka t. t. 149 0 až 150 0 Celsia, čistoty 99,93% (stanoveno plynovou chromatografií] se získá krystalizací z me-thanolu. Následující příklad přípravy sloučeniny podle vynálezu látku pouze dokládá, ale neomezuje. Příklad
Směs 16,2 g (0,10 molu) 2,6-dichlorahili-nu, 15,5 g (0,11 molu) benzoylchloridu a 50 ml pyridinu se za stálého míchání zahřívá 2 hod. na teplotu 100 °C; vzniklá hnědá reakční směs se ponechá zchladnout na 20 °C a za míchání se zředí 250 ml dest. vody. Vyloučená hnědá sraženina surového 2,6-dichloranilidu kyseliny benzoové se odsaje, promyje 150 ml dest. vody a usuší do konst. hmotnosti; získá se 22,3 g produktu tj. 82,1 % th. 98% čistoty (stanoveno plynovou chromatografií). Krystalizací surového produktu ze 150 ml methanolu se získá 17,0 g čistého (99,93%) 2,6-dichloranilidu kyseliny benzoové, bílé krystalické látky t. t. 149 c až 150 °C (Koffler).
The invention relates to benzoic acid 2,6-dichloroanilide of the formula I
which is an intermediate for the preparation of α- (2,6-di-chloroanilino) -phenylacetic acid, whose sodium salt (diclofenac sodium) is a widespread drug with an anti-inflammatory and anti-inflammatory effect.
The novel compound of formula I is prepared by reacting 2,6-dichloroaniline with benzoyl chloride in the presence of an equivalent amount of pyridine or a tertiary amine as a pro-tacceptor, at a temperature range of 20 ° to 110 ° Celsius; after diluting the reaction mixture with water, the crude benzoic acid 2,6-dichloroanilide precipitated is isolated by filtration at 147-149 ° C. Pure 2,6-dichloroanilide benzoic acid as a white crystalline solid m.p. 149-150 ° C, 99.93% purity (as determined by gas chromatography) is obtained by crystallization from methanol. Example
A mixture of 16.2 g (0.10 mol) of 2,6-dichloro-amine, 15.5 g (0.11 mol) of benzoyl chloride and 50 ml of pyridine was heated at 100 DEG C. for 2 hours with stirring; The resulting brown reaction mixture was allowed to cool to 20 ° C and diluted with 250 mL of dist. water. The precipitated brown precipitate of crude benzoic acid 2,6-dichloroanilide is filtered off with suction, washed with 150 ml of dist. water and dry to const. weight; 22.3 g of product is obtained, i.e. 82.1% th. 98% purity (as determined by gas chromatography). Crystallization of the crude product from 150 mL of methanol gave 17.0 g of pure (99.93%) benzoic acid 2,6-dichloroanilide, white crystalline solid, mp 149-150 ° C (Koffler).
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS866329A CS259821B1 (en) | 1986-09-01 | 1986-09-01 | Benzoic acid 2,6-dichloroanilide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS866329A CS259821B1 (en) | 1986-09-01 | 1986-09-01 | Benzoic acid 2,6-dichloroanilide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS632986A1 CS632986A1 (en) | 1988-03-15 |
| CS259821B1 true CS259821B1 (en) | 1988-11-15 |
Family
ID=5410078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS866329A CS259821B1 (en) | 1986-09-01 | 1986-09-01 | Benzoic acid 2,6-dichloroanilide |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS259821B1 (en) |
-
1986
- 1986-09-01 CS CS866329A patent/CS259821B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS632986A1 (en) | 1988-03-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69327890T2 (en) | Process for the preparation of 2- (un) substituted 4-alkylimidazoles | |
| SU575026A3 (en) | Method of preparing 2,6-disubstituted 2-phenyliminoimidazolidines or salts thereof | |
| JPS62238236A (en) | Production of alkoxysalicylic acid derivative | |
| JPS5916871A (en) | Sulfonamide-based benzamides | |
| US20080188667A1 (en) | Azlactone compound and method for preparation thereof | |
| SU639450A3 (en) | Method of obtaining heterogeneous ring compounds or salts thereof | |
| US4292431A (en) | Process for the production of hydroxymethylimidazoles | |
| KR20040039430A (en) | Process for producing (2-nitrophenyl)acetonitrile derivative and intermediate therefor | |
| US4107179A (en) | Method for preparing ticrynafen | |
| KR910004177B1 (en) | Anilinopyrimidine derivatives | |
| CN109553629A (en) | A kind of preparation method of Cefuroxime Sodium intermediate E type impurity compound | |
| SU1685935A1 (en) | 2-[(benzo-2 | |
| CN1360569A (en) | Method for preparation of Z-methoxy-4-(N-t-butylamino-carbonyl)benzenesulfonyl chloride | |
| US4285878A (en) | N-Phenyl-N'-cyano-O-phenylisoureas | |
| KR100207247B1 (en) | Process for the manufacture of anilinofumarate via chloromaleate or chlorofumarate or mixtures thereof | |
| SU507235A3 (en) | The method of obtaining 2n-3-isoquinolones | |
| HU209543B (en) | New method for production of alkanesulfonanilide-derivatives | |
| SU882187A1 (en) | 1,1-dioxo-3-hydroxythiolanyl-4-isothiouronic salts as initial substance for synthesis of 3,4-thriiranothiolan-1,1-dioxide | |
| SU449053A1 (en) | Method for producing 9-phenyl-11,14-dicyanoperhydroacridine derivatives | |
| SU556726A3 (en) | The method of obtaining sulfonylaminopyrimidine derivatives or their salts | |
| KR810000198B1 (en) | Method for preparing ticrynafen | |
| KR820001277B1 (en) | Process for preparation of 5-substituted picolinic acid derivatives | |
| JPS59148770A (en) | 2,4-dichloro-5-thiazole carboxaldehyde and manufacture | |
| JP2000143618A (en) | Synthetic method of asymmetric disulfide | |
| SU639878A1 (en) | Method of obtaining 6-amino-4-acylamido-2-mercaptopyrimidines |