HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-[5-(methylthio)-1,3,4-oxadiazol-2-yl]benzenemethanesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1,5-Diazabicyclo(5,4,0)undec-5-ene | HCID 314112 | — |
| Reactant | Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl ester | HCID 10945667 | — |
| Reactant | 2-[5-(Methylthio)-1,3,4-oxadiazol-2-yl]benzenemethanesulfonamide | HCID 13958777 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-[5-(methylthio)-1,3,4-oxadiazol-2-yl]benzenemethanesulfonamide | HCID 13958778 | 25.7% |
Reaction Steps
To a solution containing 0.62 g of the sulfonamide prepared in Example 3 contained in 10 ml of p-dioxane was added 0.6 g of phenyl(4,6-dimethoxy pyrimidin-2-yl)carbamate followed by dropwise addition of 0.33 g of 1,5-diazabicyclo[5.4.0]undec-5-ene (DBU). The solution was stirred at room temperature for two hours then diluted with about 100 ml of water. The clear solution was acidified with concentrated hydrochloric acid (red to litmus paper), to give a viscous oil. The oil was triturated by decanting off the aqueous solvent and stirring the oil residue in about 5 ml of acetonitrile. After filtering the suspension, the solid residue was washed with 1×5 ml of warm ethyl acetate to give 0.26 g of the subject compound; m.p. 174°-177° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04699649 |
| Source dataset | uspto-grants-1987_10 |
| ORD ID | ord-445d034cb3f3438baeb175ffb9843ee9 |
| Source note | uspto-grants-1987_10 |