HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 2-(3,4-Dimethoxy-phenyl)-N-[2-(3,4-dimethoxy-phenylsulfanyl)-ethyl]-acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | (3,4-Dimethoxyphenyl)acetyl chloride | HCID 3604458 | — |
| Reactant | 2-(3,4-Dimethoxy-phenylsulfanyl)-ethylamine | HCID 13759431 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-(3,4-Dimethoxy-phenyl)-N-[2-(3,4-dimethoxy-phenylsulfanyl)-ethyl]-acetamide | HCID 18442575 | 97.2% |
Reaction Steps
To a cold (0° C.) solution of 2-(3,4-dimethoxy-phenylsulfanyl)-ethylamine (3.97 g, 18.6 mmol) in anhydrous THF (49 ml), were added TEA (3.11 ml, 18.6 mmol) and portionwise 3,4-dimethoxyphenylacetylchloride (4.0 g, 18.6 mmol). The resulting mixture was stirred at RT for 20 h under nitrogen. The mixture was combined with H2O and extracted three times with CH2Cl2. The combined organic phases were dried over anhydrous MgSO4, filtered and concentrated to give a crude solid. Flash chromatography (AcOEt) gave the title product (7.08 g, 97%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07192950B2 |
| Source dataset | uspto-grants-2007_03 |
| ORD ID | ord-d912c89fa56e4edcb5506a9cb468c3ac |
| Source note | uspto-grants-2007_03 |