Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | N,N-Diphenylcarbamic chloride | HCID 65741 | — |
| Reactant | 3-Quinolin-3-ylprop-2-yn-1-ol | HCID 650142 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | tert-Butyl methyl ether | HCID 15413 | — |
| Product | HCID 66669477 | HCID 66669477 | — |
Reaction Steps
To a dry three-necked round-bottom flask equipped with nitrogen inlet and overhead stirrer was charged 3-(3-quinolyl)-2-propyn-1-ol (5 g, 27 mmol) in THF (50 ml) and the solution was cooled to 0° C. Potassium t-butoxide (3.6 g, 32 mmol) was then added followed by diphenylcarbamoyl chloride (6.9 g, 29.7 mmol). The mixture was stirred for 2 hours at 0° C. and then allowed to warm up to room temperature over a period of 6 hours by which time the reaction was determined to be complete. The reaction mixture was worked up with MTBE (100 ml) and 10% NH4Cl (50 ml) and was concentrated to ¼ the volume. Heptane (75 ml) was added and the product was crystallised out. Yield=8.3 g (80%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06417366B2 |
|---|
| Source dataset | uspto-grants-2002_07 |
|---|
| ORD ID | ord-2b005e77eb3b4f58982663b33d3bc7e6 |
|---|
| Source note | uspto-grants-2002_07 |
|---|