HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methoxyphenol → N-[4-(4-Methoxy-phenoxy)-phenyl]-methanesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methoxyphenol | HCID 9015 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | N,N-Dimethylglycine hydrochloride | HCID 75605 | — |
| Reactant | N-(4-iodophenyl)methanesulfonamide | HCID 836147 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | N-[4-(4-Methoxy-phenoxy)-phenyl]-methanesulfonamide | HCID 68517759 | — |
Reaction Steps
A mixture of N-(4-iodo-phenyl)-methanesulfonamide (0.45 g, 1.52 mmol) from Step A, 4-methoxyphenol (0.28 g, 2.28 mmol), Cs2CO3 (0.99 g, 3.04 mmol), N,N-dimethylglycine HCl salt (31.8 mg, 0.23 mmol) and CuI (14.5 mg, 0.076 mmol) in dioxane (4 mL) under N2 was heated to 100 C overnight. The reaction was diluted with EtOAc and brought to the usual work-up. The residue was purified by chromatography (silica gel, 30% EtOAc/hexanes) to give the desired product. MS (EI) 294 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07803793B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-a9c8034169a948b183255b3372e04166 |
| Source note | uspto-grants-2010_09 |