HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → {1-[4-(2-Phenyl-4-thioxo-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Lawesson's reagent | HCID 87949 | — |
| Reactant | {1-[4-(4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester | HCID 67067804 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Cyclohexane | HCID 8078 | — |
| Product | {1-[4-(2-Phenyl-4-thioxo-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester | HCID 86671045 | 185.6% |
Reaction Steps
To a solution of {1-[4-(4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (30 mg, 0.0642 mmol) in toluene (3 mL) was added Lawesson's reagent (2,4-bis-(4-methoxy-phenyl)-[1,3,2,4]dithiadiphosphetane 2,4-disulfide) (15.6 mg, 0.039 mmol). The reaction mixture was heated at reflux for 3 hours. The cooled mixture was subjected to flash chromatography (SiO2, 20% EtOAc in cyclohexane). A second chromatography (SiO2, 3% EtOAc in toluene) afforded the title compound (35 mg). LCMS (Method A): RT=5.08 min, [M+H]+=484.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08546376B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-fe1858bbca4646f1bb35de4b3f21fb73 |
| Source note | uspto-grants-2013_10 |