HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → N-(4-bromo-3-chlorophenyl)methanesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | 4-Bromo-3-chloroaniline | HCID 88888 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N-(4-bromo-3-chlorophenyl)methanesulfonamide | HCID 22193858 | 21.1% |
Reaction Steps
To a solution of Intermediate 62A (0.843 g, 4.08 mmol) in THF (20.41 mL) was added triethylamine (5.69 mL, 40.8 mmol) followed by methanesulfonyl chloride (0.414 mL, 5.31 mmol). The reaction mixture was allowed to stir at room temperature for 3 days, then quenched with a saturated aqueous solution of NaHCO3 and diluted with EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc (2×). The organic phases were combined, dried over Na2SO4, filtered, and concentrated to afford the title compound (245 mg, 0.861 mmol, 21.09% yield) as a white solid. HPLC Ret timej: 1.32 min. MS (ES): m/z=284.2 [M+H]−. Intermediate 62 was used in the synthesis of Example 212.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08916553B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-2c2e4693017549848056480b352c7ce9 |
| Source note | uspto-grants-2014_12 |