HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-(2-Benzothienyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-[(2-Benzothienylcarbonyl)amino]cyclohexanecarboxylic acid | HCID 43242040 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-(2-Benzothienyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one | HCID 57672854 | 76.7% |
Reaction Steps
4.1 g (21 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 5 g (16 mmol) of 1-[(2-benzothienylcarbonyl)amino]cyclohexanecarboxylic acid in 50 ml of methylene chloride. After the mixture was stirred at room temperature for 4 hours, the reaction solution was concentrated under reduced pressure, ethyl acetate was added thereto, and the mixture was successively washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and saturated brine. The organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to obtain 3.5 g (75%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08829209B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-48bf78085dae40148953adac9135e237 |
| Source note | uspto-grants-2014_09 |