HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 5-Chloro-2-methoxy-N-(2-(1-(3-isopropylthioureidosulfonyl)piperidin-4-yl)ethyl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Isopropyl Isothiocyanate | HCID 75263 | — |
| Reactant | 4-(2-(5-Chloro-2-methoxybenzamido)ethyl)piperidine-1-sulfonamide | HCID 12282030 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | 5-Chloro-2-methoxy-N-(2-(1-(3-isopropylthioureidosulfonyl)piperidin-4-yl)ethyl)benzamide | HCID 11518556 | 60% |
Reaction Steps
188 mg (0.5 mmol) of 4-(2-(5-chloro-2-methoxybenzamido)ethyl)piperidine-1-sulfonamide and 326 mg (1 mmol) of cesium carbonate were heated in 5 ml of N-methyl-2-pyrrolidone with 0.1 ml (0.9 mmol) of isopropyl isothiocyanate at 80° C. for 10 minutes. The reaction mixture was poured onto ice/2 M hydrochloric acid and extracted three times with 10 ml of dichloromethane each time. The combined organic phases were dried over sodium sulfate and filtered after addition of activated carbon. The crude product obtained after removal of the solvent was recrystallized from methanol. 142 mg (60%) of the title compound were obtained as a colorless solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08586612B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-d9484b6b11754664b874ae0ba8078f6f |
| Source note | uspto-grants-2013_11 |