Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Resorcinol | HCID 5054 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-[(2-Tert-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propyl 4-methylbenzenesulfonate | HCID 86625867 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 11647656 | HCID 11647656 | 41% |
Reaction Steps
A mixture of 3-[(2-tert-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propyl 4-methylbenzenesulfonate (0.045 g, 0.091 mmol), resorcinol (0.020 g, 0.183 mmol) and K2CO3 (0.063 g, 0.457 mmol) in MeCN (2 ml) was heated in a microwave reactor at 120° C. for 10 mins. The reaction mixture was evaporated and the residue was purified by silica gel column chromatography (Horizons Biotage) using 0-50% EtOAc in DCM as eluent to give the title compound (0.016 g, 41%) as a solid. 1H NMR (500 MHz CDCl3): δ 7.54-7.48 (m, 2H), 7.46-7.41 (m, 3H), 7.13 (t, 1H), 6.46-6.41 (m, 2H), 6.39-6.36 (m, 1H), 5.75 (t, 1H), 5.14 (s, 1H), 3.86 (t, 2H), 3.11-3.04 (m, 2H), 1.86-1.78 (m, 2H), 1.75 (s, 9H); 13C NMR (125 MHz CDCl3): 159.9, 157.1, 135.4, 131.8, 130.4, 129.8, 128.8, 125.3, 108.5, 107.1, 106.9, 102.3, 66.1, 61.8, 42.5, 28.9, 27.8; Mass Spectrum: M+H+ 431.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07723333B2 |
|---|
| Source dataset | uspto-grants-2010_05 |
|---|
| ORD ID | ord-f7e5ac8a978e4e929fe56710b8d6889f |
|---|
| Source note | uspto-grants-2010_05 |
|---|