Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | 1-Benzyl-1H-pyrazol-5-amine | HCID 77061 | — |
| Reactant | Sodium Nitrite | HCID 23668193 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | HCID 86718549 | HCID 86718549 | — |
Reaction Steps
p-Toluenesulfonic acid (29.82 g; 0.17 mol) was stirred in 150 ml ACN. 2-Benzyl-2H-pyrazol-3-ylamine (10.0 g; 0.06 mol) was added and cooled down to 10-15° C. Sodium nitrite (7.97 g; 0.12 mol) was dissolved in 15.0 ml water and added. The resulting mixture was stirred for 1 hour at 0° C. In 30 ml of water was dissolved potassium iodide (23.96 g; 0.14 mol) and added at 0° C. The reaction mixture was stirred at ambient temperature for 6 hours. It was diluted with 100 ml water and neutralized with NaHCO3 solution, then extracted with DCM. The organic layers were pooled and washed with sodium thiosulfate, dried and evaporated. The crude material was purified with normal phase chromatography (2% EtOAc/Hexane).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09422290B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-5b910fb823414625b95b6588419071a1 |
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| Source note | uspto-grants-2016_08 |
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