HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Butyn-2-ol → 4,5-dihydro-3-(3-hydroxy-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Butyn-2-ol | HCID 16239 | — |
| Reactant | 4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one | HCID 19830677 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Diethylamine | HCID 8021 | — |
| Product | 4,5-dihydro-3-(3-hydroxy-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one | HCID 19851601 | — |
Reaction Steps
6.78 g (20 mmol) of 4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one was heated to boiling under reflux for 7 hours with 1.75 g (25 mmol) of 3-butyn-2-ol, 70 mg of bis-(triphenylphosphine)-palladium(II) dichloride and 15 mg of copper(I) iodide in 50 ml of diethylamine and 30 ml of ethylene chloride. The reaction mixture was evaporated and the residue was chromatographed on silica gel while eluting with ethyl acetate. After recrystallization from ethyl acetate and hexane there was obtained 4,5-dihydro-3-(3-hydroxy-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 161°-162°.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04863920 |
| Source dataset | uspto-grants-1989_09 |
| ORD ID | ord-42dcc1251104485b85e9527b922b46f9 |
| Source note | uspto-grants-1989_09 |