HuagongsheHuagongshe Chemistry Print Report · For research reference only
Thionyl Chloride → 1-[2-Chloro-4-(4-chlorophenyl)butyl]-1H-imidazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | Butoconazole nitrate | HCID 47471 | — |
| Reactant | 1-[4-(Chlorophenyl)-2-hydroxy-n-butyl]-imidazole | HCID 69055504 | — |
| Product | 1-[2-Chloro-4-(4-chlorophenyl)butyl]-1H-imidazole | HCID 12432034 | — |
Reaction Steps
in the presence of sodium hydride reagent in dimethylformamide solvent. This substitution reaction takes a long time and gives the (1-[4-(4-chlorophenyl)-2-hydroxy-n-butyl]-imidazole) (IV) with a poor yield (51.7%). In the next step of the butoconazole nitrate synthesis (1-[4-(chlorophenyl)-2-hydroxy-n-butyl]-imidazole) (IV) is treated with thionyl chloride (which is at once a reagent and a solvent) at 65-70° C. to yield 1-[4-(4-chlorophenyl)-2-chloro-n-butyl]-imidazole of the formula (V).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07625935B2 |
| Source dataset | uspto-grants-2009_12 |
| ORD ID | ord-34ecd88d3223437283e508490c080bb9 |
| Source note | uspto-grants-2009_12 |