Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Isobutylene oxide | HCID 11208 | — |
| Reactant | 4-nitro-1H-pyrazole | HCID 16376 | — |
| Reactant | 1,8-Diazabicycloundec-7ene | HCID 129662960 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 60886989 | HCID 60886989 | 73% |
Reaction Steps
To a solution of 4-nitro-1H-pyrazole (1 equiv) in acetonitrile (1 M) was added 1,8-diazabicycloundec-7ene (2 equiv) and 1,2-epoxy-2-methylpropane (3.2 equiv). The reaction mixture was stirred at 60° C. for 20 h. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate. The organic solution was washed with HCl (1 N), water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound which was directly used in the next step without further purification (73% yield). 1H NMR (400 MHz, CHLOROFORM-d1) δ ppm 8.26 (s, 1H), 8.09 (s, 1H), 4.13 (s, 2H), 2.64 (s, 1H) 1.24 (s, 6H). MS (ESI) m/z 186.2 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09428509B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-9ee7837648134630be39c6d959c7a0b9 |
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| Source note | uspto-grants-2016_08 |
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