Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetone | HCID 180 | — |
| Reactant | 4-Toluenesulfonyl chloride | HCID 7397 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 3-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-7-fluoroindolin-2-one | HCID 67982437 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 86707248 | HCID 86707248 | 23.3% |
Reaction Steps
3-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-7-fluoro-1,3-dihydro-2H-indol-2-one (1.15 g), 4-methylbenzenesulfonyl chloride (1.06 g) and sodium carbonate (0.41 g) are introduced as initial charge in 5.5 ml of water and 11 ml of acetone and, with stirring, heated to 80° C. in a preheated oil bath. After 45 minutes, the hot solution is filtered, and the solid is washed with 20 ml of water/acetone (1:1) and methanol and dried in vacuo. This gives 0.76 g of product in an HPLC purity of 97% (42% of theory). Structure elucidation by NMR verifies that it is the O-sulfonylated product. A further 0.41 g of product in an HPLC purity of 89% can be isolated from the filtrate (21% of theory).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08969553B2 |
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| Source dataset | uspto-grants-2015_03 |
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| ORD ID | ord-9514c0896c644b0a98cd85a6e33c0b62 |
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| Source note | uspto-grants-2015_03 |
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