HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 7-(5-Chloro-2-methoxyphenyl)-8-chloromethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | 7-(5-Chloro-2-methoxyphenyl)-8-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one | HCID 57671785 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 7-(5-Chloro-2-methoxyphenyl)-8-chloromethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one | HCID 57671764 | 81% |
Reaction Steps
7-(5-Chloro-2-methoxyphenyl)-8-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 13-1, 1.34 g, 3.71 mmol) was dissolved in anhydrous dichloromethane (19 mL), and triethylamine (621 μL, 4.46 mmol) and methanesulfonyl chloride (316 μL, 4.08 mmol) were added thereto successively. The reaction mixture was stirred at room temperature overnight. Ethyl acetate (200 mL) was added to the reaction mixture, washed with water (200 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (1.14 g) as a colorless amorphous product. (Yield 81%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08975256B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-24505f1017e6472482e9861579dc86e9 |
| Source note | uspto-grants-2015_03 |