HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phthalimide potassium salt → 2-[2-(4-Chloro-phenyl)-2-hydroxy-2-(4-iodo-phenyl)-ethyl]-isoindole-1,3-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phthalimide potassium salt | HCID 24194345 | — |
| Reactant | 2-(4-Chlorophenyl)-2-(4-iodophenyl)oxirane | HCID 59317217 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-[2-(4-Chloro-phenyl)-2-hydroxy-2-(4-iodo-phenyl)-ethyl]-isoindole-1,3-dione | HCID 59331969 | 34% |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
A mixture of 2-(4-chloro-phenyl)-2-(4-iodo-phenyl)-oxirane* (571 mg, 1.60 mmol) and potassium phthalimide (340 mg, 1.84 mmol) in THF (5 mL) and DMSO (2 mL) was heated at 100° C. for 20 hours. The mixture was concentrated in vacuo, diluted with ethyl acetate and washed with water and brine (×2), dried (MgSO4), filtered and concentrated to give a crude product which was purified by column chromatography (SiO2), eluting with a gradient of ethyl acetate/petrol (2.5% to 100%) then 10% methanol/dichloromethane to give the title compound (273 mg, 34%); LCMS (PS-A2) Rt 3.22 min [M+H]+504. *This starting material can be made by the method described in Example 79A
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08343953B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-974cfdcf8430430796b143d88ac9eb72 |
| Source note | uspto-grants-2013_01 |