HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sulfuric Acid → 3-(3-Imidazol-1-yl-phenyl)-3-oxo-propionic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Lithium Bromide | HCID 82050 | — |
| Reactant | 3-(1H-imidazol-1-yl)benzoic acid | HCID 2795544 | — |
| Reactant | 2,2-Bis(trimethylsilyl)propanedioate | HCID 22224580 | — |
| Reactant | 3-(1H-imidazol-1-yl)benzoyl chloride hydrochloride | HCID 22224590 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Isopropenyl acetate | HCID 7916 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 3-(3-Imidazol-1-yl-phenyl)-3-oxo-propionic acid | HCID 22224638 | — |
| Product | 6-(3-Imidazol-1-yl-phenyl)-2,2-dimethyl-[1,3]dioxin-4-one | HCID 22224895 | — |
Reaction Steps
The 3-(3-imidazol-1-yl-phenyl)-3-oxo-propionic acid was prepared from 3-(1H-imidazol-1-yl)benzoyl chloride hydrochloride [prepared by treatment of 3-(1H-imidazol-1-yl)-benzoic acid (J. Med. Chem. 1987, 30, 1342; CAS-No. [108035-47-8] with SOCl2) and bis(trimethylsilyl)malonate with Et3N and LiBr in CH3CN at 0° C. according to general procedure K (method cl). The crude material was transformed into the title compound by stirring in isopropenyl acetate and conc. H2SO4 according to general procedure L (method a). Obtained as an orange semisolid (617 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06544985B2 |
| Source dataset | uspto-grants-2003_04 |
| ORD ID | ord-269cf5f8beba44f6b87931cc274a6ac6 |
| Source note | uspto-grants-2003_04 |