HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 5-Cyano-1-(2,4-dimethoxybenzenesulfonyl)-3-hydroxy-3-(2-ethoxyphenyl)-indol-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | 2,4-Dimethoxybenzenesulfonyl chloride | HCID 2734626 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | 5-Cyano-3-(2-ethoxyphenyl)-3-hydroxy-indol-2-one | HCID 66593041 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-Cyano-1-(2,4-dimethoxybenzenesulfonyl)-3-hydroxy-3-(2-ethoxyphenyl)-indol-2-one | HCID 66592993 | 49.1% |
Reaction Steps
1.7 g (15 mmol) of potassium tert-butanolate were added in portions to 4 g (13.6 mmol) of the intermediate 1b in 40 ml of anhydrous dimethylformamide at 0° C., and the mixture was stirred for about 90 minutes. Then 3.4 g (14.3 mmol) of 2,4-dimethoxybenzenesulfonyl chloride were rapidly added dropwise at 0° C. The reaction mixture was stirred at 0° C. for 2 h. This solution was then poured into an ice-water/K2CO3 solution, resulting in a precipitate which was isolated. The resulting residue was treated with a little methanol, filtered off with suction and dried, resulting in 3.3 g of the product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08129389B2 |
| Source dataset | uspto-grants-2012_03 |
| ORD ID | ord-abffd40b5f6044ca92618cb63502bc76 |
| Source note | uspto-grants-2012_03 |