HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 1-(3-Methyl-benzo[d]isoxazol-6-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 1-[3-Fluoro-4-(1-hydroxyimino-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one | HCID 86649397 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-(3-Methyl-benzo[d]isoxazol-6-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one | HCID 59636184 | 10.7% |
Reaction Steps
NaH (32.8 mg, 1.3705 mmol) and DMF (4 mL) was added to 1-[3-fluoro-4-(1-hydroxyimino-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (111b: 150 mg, 0.4568 mmol). The resulting mixture was microwaved at 50° C. for 1 hour. The reaction was monitored by TLC (10% MeOH in DCM). The reaction mixture was partitioned between ice water and ethylacetate. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated under reduced pressure. Purification by column chromatography on silica gel (5% MeOH in CHCl3) afforded 15 mg of the product (10.7% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | USRE045173E1 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-c7fdfbe7151a4b099a1dd4d5e3b16cc3 |
| Source note | uspto-grants-2014_09 |