N,N-Dimethylaniline → HCID 86667783, compound

To a stirred suspension of 7-trifluoromethyl-1H-quinazoline-2,4-dione (25 g, 0.11 mol) and N,N-dimethylaniline (13.1 g, 0.11 mol) at 0° C. was added phosphorus oxychloride (101 mL, 1.1 mol) and the reaction mixture was heated at reflux for 6 h. The reaction mixture was allowed to cool to room temperature then concentrated under reduced pressure. The resultant solid was dissolved in THF (50 mL) then cooled to 0° C. and a solution of ethylamine (10 mL, 2 molar in THF) was added dropwise with stirring. After 2 h, the reaction mixture was concentrated under reduced pressure, diluted with water (250 mL) and extracted with ethyl acetate (2×150 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. Yield=14 g, 47%; LC-MS: 3.1 min, 276 (M+); 1H NMR (DMSO-d6): δ 1.26 (apparent t, 3 H, J=7 Hz), 3.57 (ddd, 2H, J=12.7, 7.3, 5.6 Hz), 7.84 (dd, 1 H, J=8.7, 1.6 Hz), 7.93 (s, 1 H), 8.49 (d, 1 H, J=8.7 Hz), 9.05 (apparent t, 1 H, J=5 Hz).

1. temperaturethe reaction mixture was heated
2. temperatureat reflux for 6 h
3. concentrationthen concentrated under reduced pressure
4. dissolutionThe resultant solid was dissolved in THF (50 mL)
5. temperaturethen cooled to 0° C.
6. additiona solution of ethylamine (10 mL, 2 molar in THF) was added dropwise
7. concentrationthe reaction mixture was concentrated under reduced pressure
8. additiondiluted with water (250 mL)
9. extractionextracted with ethyl acetate (2×150 mL)
10. dry with materialThe combined organic layers were dried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure
13. custom3.1 min, 276 (M+)

ORD record

ord-f9be277bc53d48f399c5774efe950977

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796180B2