HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanesulfonic Acid → 3-((3-(4-Chloro-2-hydroxyphenyl)-1,2,4-thiadiazol-5-yl)methoxy)-2,6-difluorobenzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanesulfonic Acid | HCID 6395 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 3-((3-(2-(Benzyloxy)-4-chlorophenyl)-1,2,4-thiadiazol-5-yl)methoxy)-2,6-difluorobenzamide | HCID 59549535 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-((3-(4-Chloro-2-hydroxyphenyl)-1,2,4-thiadiazol-5-yl)methoxy)-2,6-difluorobenzamide | HCID 135872733 | 30.2% |
Reaction Steps
To a solution of 3-((3-(2-(benzyloxy)-4-chlorophenyl)-1,2,4-thiadiazol-5-yl)methoxy)-2,6-difluorobenzamide (0.05 g, 0.10 mmol) in dichloromethane (5 ml) was added methanesulfonic acid (0.50 ml, excess) at room temperature under nitrogen atmosphere and allowed to stir at same temperature for 90 min. After the completion of the reaction (TLC monitoring), the solution was cooled to 0° C. and basified with saturated NaHCO3 solution (aqueous) followed by extraction with EtOAc (3×25 ml). The combined organics was dried over anhydrous Na2SO4, filtered and concentrated. The residue was washed with ether to get the desired product (0.012 g, 30%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08492414B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-b2a9751877294b129ea2d909eee6264a |
| Source note | uspto-grants-2013_07 |