HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-methyl-1H-pyrazole-3-carboxylic acid → 5-(5-methyl-1H-pyrazol-3-yl)-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 5-methyl-1H-pyrazole-3-carboxylic acid | HCID 9822 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 4-(Trifluoromethoxy)benzamidoxime | HCID 2733309 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-(5-methyl-1H-pyrazol-3-yl)-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole | HCID 46901654 | — |
Reaction Steps
To a mechanically stirred solution of 5-methyl-1H-pyrazole-3-carboxylic acid (15.3 g, 0.121 mol) in dry DMF (600 mL) was added EDCl (23.3 g, 0.121 mol), HOBT (16.4 g, 0.121 mol) and N′-hydroxy-4-(trifluoromethoxy)benzenecarboximidamide (26.7 g, 0.121 mol). The mixture was stirred at rt for 2 h, and then warmed to 140° C. and stirred for further 5 h. After being cooled to rt, the mixture was diluted with water (2 L) and extracted with ethyl acetate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08796253B2 |
| Source dataset | uspto-grants-2014_08 |
| ORD ID | ord-6b62cae143dd4f87a1f53fb7529e54c6 |
| Source note | uspto-grants-2014_08 |