Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Phthalimide | HCID 6809 | — |
| Reactant | Potassium | HCID 5462222 | — |
| Reactant | 4-(ChloroMethyl)-2-cyclopropyloxazole | HCID 58044319 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66678607 | HCID 66678607 | 51.4% |
Reaction Steps
To the stirred solution of 4-chloromethyl-2-cyclopropyl-oxazole (4.0 g, 25.38 mmol) in dry DMF (30 mL), was added potassium salt of phthalimide (4.7 g, 25.38 mmol) at rt. The resulting mixture was stirred for 24 h at rt and monitored through TLC. After completion of the reaction, water (200 mL) was added and the crude was extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtained crude residue which was purified via column chromatography (100-200 silica gel, elution with 20% EtOAc in hexane). 3.5 g of 2-(2-cyclopropyl-oxazol-4-ylmethyl)-isoindole-1,3-dione was obtained as a white solid, 269.2 (M+H)+, which contained phthalimide. This compound was used for the next step as such.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08729105B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-0c7131cfe2c74192b2e594d79f1fa657 |
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| Source note | uspto-grants-2014_05 |
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