HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → HCID 57458240, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 3-Bromobenzene-1-sulfonamide | HCID 2734765 | — |
| Catalyst | Triphenylphosphine | HCID 11776 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 57458240 | HCID 57458240 | 85.3% |
Reaction Steps
A dimethylformamide (30 mL) solution of 3-bromobenzenesulfonamide (13.7 g), trimethylsilylacetylene (5.18 g), copper(I) iodide (65 mg), bis(triphenylphosphine)palladium(II) dichloride (400 mg), triphenylphosphine (300 mg) and triethylamine (15.0 mL) was stirred at 80° C. for 6 hours. Thereafter, the reaction solution was added to water, and the obtained solution was then extracted with ethyl acetate. The organic layer was successively washed with water and a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel 60 N, hexane:ethyl acetate=4:1 to 3:1), so as to obtain the title compound (11.4 g) in the form of a light brown solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08642626B2 |
| Source dataset | uspto-grants-2014_02 |
| ORD ID | ord-637e17ccc9364bf2855e2fd9fbcee922 |
| Source note | uspto-grants-2014_02 |