HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 5-Chloro-2-methoxy-N-(2-(1-(3-propylthioureidosulfonyl)piperidin-4-yl)ethyl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Propyl Isothiocyanate | HCID 69403 | — |
| 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-propylthioureidosulfonyl)piperidin-4-yl)ethyl)benzamide | HCID 59660706 | 33% |
Reaction Steps
376 mg (1 mmol) of 4-(2-(5-chloro-2-methoxybenzamido)ethyl)piperidine-1-sulfonamide and 652 mg (2 mmol) of cesium carbonate were heated in 5 ml of N-methyl-2-pyrrolidone with 0.2 ml (1.8 mmol) of n-propyl isothiocyanate at 80° C. for 10 minutes. The reaction mixture was poured onto ice/2 M hydrochloric acid, and the precipitated solid was filtered off with suction and washed with water until neutral. The crude product obtained after purification by chromatography (silica gel; toluene/ethanol/ethyl acetate 8/1/1) was crystallized from ethyl acetate. 155 mg (33%) 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-848a96a52f05480bbf711c2aae333645 |
| Source note | uspto-grants-2013_11 |