Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | p-Fluoronitrobenzene | HCID 9590 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Diallylamine | HCID 31279 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 11579422 | HCID 11579422 | 59.5% |
Reaction Steps
A mixture of 4-fluoronitrobenzene (5.00 g, 35.44 mmol), diallylamine (3.48 g, 4.4 ml, 35.44 mmol) and K2CO3 (5.39 g, 38.98 mmol) in dry DMSO (40 ml) was heated at 100° C. under an atmosphere of argon for 3 h. The reaction mixture was then left to cool to room temperature (23° C.) and added to water (300 ml) and extracted with EtOAc (4×75 ml). The combined organics were washed with brine (100 ml) and dried (Na2SO4). The solvent was removed under reduced pressure to give a red oil that was purified by chromatography (2:1 Hexane/DCM) to give the title compound (4.60 g, 59%) as an orange oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08691979B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-4fe3581bd214407da091a40a348182e1 |
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| Source note | uspto-grants-2014_04 |
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