Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | tert-Butyl methyl malonate | HCID 2733872 | — |
| Reactant | 5-Chloro-N,N-dimethyl-2-nitrobenzamide | HCID 22934807 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68760855 | HCID 68760855 | 80.5% |
Reaction Steps
Sodium hydride (350 mg) was dissolved in dimethylformamide (10 mL)), and the solution was cooled to 0° C. After addition of tert-butyl methyl malonate (1.52 g), the mixture was stirred for one hour, and the 5-chloro-N,N-dimethyl-2-nitrobenzamide (1.0 g) obtained in Example 2a) was added thereto. The mixture was stirred at 70° C. for 4.5 hours and water was added thereto. The resulting solution was concentrated, diluted with ethyl acetate and washed with water. The organic layer was dried over sodium sulfate and purified by column chromatography on silica gel with ethyl acetate:hexane=1:1 to give the title compound (1.29 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07538140B2 |
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| Source dataset | uspto-grants-2009_05 |
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| ORD ID | ord-e35f076fe60b47d98db6c6cc01f6b664 |
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| Source note | uspto-grants-2009_05 |
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