HuagongsheHuagongshe Chemistry Print Report · For research reference only
N,N-Dimethylaniline → 6-Bromo-4-chloro-2-(2-methoxyphenyl)quinazoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N,N-Dimethylaniline | HCID 949 | — |
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | 6-Bromo-2-(2-methoxy-phenyl)-3h-quinazolin-4-one | HCID 136121404 | — |
| Solvent | Benzene | HCID 241 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 6-Bromo-4-chloro-2-(2-methoxyphenyl)quinazoline | HCID 58010904 | — |
Reaction Steps
6-Bromo-2-(2-methoxyphenyl)quinazolin-4(3H)-one (674 mg, 2.0 mmol), POCl3 (624 mg, 4 mmol), and N,N-dimethylaniline (740 mg, 6.1 mmol) were dissolved in benzene (12 mL) and refluxed for 3 h. The reaction mixture was diluted with EtOAc, and the organic phase was washed with aqueous saturated NaHCO3 (1×) and H2O (2×), dried over Na2SO4, and concentrated. Purification via silica gel chromatography using 0-5% EtOAc in CH2Cl2/hexanes (1:1) gave 6-bromo-4-chloro-2-(2-methoxyphenyl)quinazoline. LC/MS: m/z 348.9 (M+H)+ at 3.66 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07928107B2 |
| Source dataset | uspto-grants-2011_04 |
| ORD ID | ord-bc610a5237e8420b986884c2c6aeb877 |
| Source note | uspto-grants-2011_04 |