HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Hydroxide → Sertaconazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | (+-)-alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol | HCID 32238 | — |
| Reactant | Sertaconazole Nitrate | HCID 200103 | — |
| Reactant | 3-(Bromomethyl)-7-chloro-1-benzothiophene | HCID 11379988 | — |
| Catalyst | Tetrabutylammonium Chloride | HCID 70681 | — |
| Solvent | Toluene water | HCID 22272177 | — |
| Product | Sertaconazole | HCID 65863 | — |
Reaction Steps
The specification CN 1358719 (CAPLUS 2003:711267) discloses the synthesis of sertaconazole mononitrate (I) by etherifying 3-bromomethyl-7-chlorobenzo[b]thiophene (III) with 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-ethanol (II) at a molar ratio of 1:1 in toluene-water (3:1, v/v) in the presence of sodium hydroxide and 50% tetrabutylammonium chloride (IV, Z═Cl) solution at 80° C. for 4 hours, extracting with ethyl ether to obtain free base of sertaconazole, salifying with nitric acid and recrystallizing in 95% ethanol. The resulting content in sertaconazole mononitrate of the thus prepared product is >98.5%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07829726B2 |
| Source dataset | uspto-grants-2010_11 |
| ORD ID | ord-7220f8852a7f442c812ae69241ac006e |
| Source note | uspto-grants-2010_11 |