Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | tert-Butyl methylsulfonylcarbamate | HCID 10081367 | — |
| Reactant | HCID 22119928 | HCID 22119928 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86756093 | HCID 86756093 | 78.7% |
Reaction Steps
tert-Butyl(methylsulfonyl)carbamate (1.52 g, 0.00780 mol) is added to a mixture of sodium hydride (60%, 0.312 g, 0.00780 mol) and tetrahydrofuran at 0° C. The mixture is allowed to come to room temperature. A solution of 3-[3-(bromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (3.00 g, 0.00714 mol) in dimethyl sulfoxide is added dropwise. The resultant mixture is stirred overnight at room temperature, poured into dilute hydrochloric acid, and extracted with methylene chloride. The combined organic layers are washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The resultant residue is chromatographed on silica gel with ether:methylene chloride to give the title compound as a white solid (3.00 g, 78.7%, mp 109-111° C.) which is identified by NMR spectral analysis.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06156700 |
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| Source dataset | uspto-grants-2000_12 |
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| ORD ID | ord-b2a6c453629b4f90a6b4d03d0bc26bc0 |
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| Source note | uspto-grants-2000_12 |
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