Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Sodium Azide | HCID 33557 | — |
| Reactant | HCID 58458581 | HCID 58458581 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 178452605 | HCID 178452605 | 47.4% |
Reaction Steps
To a solution of tert-butyl (1-(4-cyanophenyl)cyclopropyl)carbamate (D15) (1.5 g, 5.81 mmol) in dimethylformamide (15 ml), NH4Cl (530 mg, 9.90 mmol) was added under nitrogen atmosphere, followed by addition of sodium azide (650 mg, 9.9 mmol). The reaction mixture was heated to 100° C. overnight, then cooled to room temperature with ice-water bath. Water and ethylacetate (100 ml) was added. The organic layer was separated and the solvent was removed. The residue was purified by column chromatography eluting with a mixture petroleum ether/ethyl acetate (1:1). Collected fractions after solvent evaporation afforded the title compound (D16) (830 mg) as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08828987B2 |
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| Source dataset | uspto-grants-2014_09 |
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| ORD ID | ord-131f1d9e4c2b4c859a3d87f36c0fb836 |
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| Source note | uspto-grants-2014_09 |
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