HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → N-[6-(2-Benzyloxy-ethylamino)-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 2-(Benzyloxy)ethanamine | HCID 533868 | — |
| Reactant | N-(6-fluoro-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide | HCID 58964482 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | N-[6-(2-Benzyloxy-ethylamino)-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide | HCID 11525208 | 58.1% |
Reaction Conditions
| Temperature | 120 °C |
|---|
Reaction Steps
A mixture of 318 mg (1 mmol) of N-(6-fluoro-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide, 605 mg (4.0 mmol) of 2-benzyloxy-ethylamine and 3.2 ml of ethanol is heated at 120° C. in a closed vial in a microwave reactor for 10 minutes. After cooling to room temperature, 1M aqueous hydrochloric acid is added until a pH value of ˜3 is reached. The resulting mixture is extracted with ethyl acetate. The organic phase is separated, washed with water and brine, dried over magnesium sulfate and evaporated. Chromatography of the residue on silica with dichloro-methane-methanol (93:7) and crystallization from tetrahydrofuran-hexane gives 261 mg (58%) of the title compound as red crystals, m.p. 204° C. (decomp.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08299085B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-b81c41d409554f45af7d71a3e70330f8 |
| Source note | uspto-grants-2012_10 |