Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | 6-Methoxy-7-[2-(2-methoxyethoxy)ethoxy]quinazolin-4(1H)-one | HCID 135742285 | — |
| Product | HCID 22030960 | HCID 22030960 | 87% |
Reaction Steps
A solution of 6-methoxy-7-(2-(2-methoxyethoxy)ethoxy)quinazolin-4-one (930 mg, 3.2 mmol) in thionyl chloride (15 ml) containing DMF (150 μl) was heated at 60° C. for 1.5 hours. The volatiles were removed by evaporation. The residue was dissolved in methylene chloride, the solution was cooled to 5° C. and adjusted to pH8 by the addition of 5% aqueous sodium hydrogen carbonate solution. The organic layer was separated, washed with brine, dried (MgSO4), filtered and the volatiles were removed under vacuum. The residue was purified by column chromatography eluting with ethyl acetate to give 4-chloro-6-methoxy-7-(2-(2-methoxyethoxy)ethoxy)quinazoline (863 mg, 87%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06294532B1 |
|---|
| Source dataset | uspto-grants-2001_09 |
|---|
| ORD ID | ord-6b563befe34843d6b951ef7dab9aa110 |
|---|
| Source note | uspto-grants-2001_09 |
|---|