Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2,6-Lutidine | HCID 7937 | — |
| Reactant | Triethylsilyl trifluoromethanesulphonate | HCID 2733308 | — |
| Reactant | HCID 178513825 | HCID 178513825 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178477544 | HCID 178477544 | 67.7% |
Reaction Steps
A stirred mixture of 1H-1,2,4-triazole-3-carboxamide (500 mg, 4.46 mmol) in 1,2-dichloroethane (4.46 mL) treated at room temperature with 2,6-lutidine (2.08 mL, 17.84 mmol) and triethylsilyl trifluoromethanesulfonate (3.03 mL, 13.38 mmol) and heated under a nitrogen atmosphere at 50° C. After 4 hours of heating the reaction solution allowed to cool to room temperature and diluted with dichloromethane (25 mL), washed with water (25 mL), 0.5M hydrochloric acid (25 mL), water (25 mL), dried over MgSO4, filtered, and evaporated to solid. The solid was flash chromatographed (silica gel, 10-65% ethyl acetate:hexane) to give the product as a white solid (683 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08188085B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-b59cfd08d5804f0db8f61d58a53ad391 |
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| Source note | uspto-grants-2012_05 |
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