Dimethylformamide → 6-Bromo-4-chloro-2-(2-fluorophenyl)quinazoline

HRID 457716Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])[NH:6][C:5]2=O.S(Cl)([Cl:22])=O.CN(C)C=O>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])[N:6]=[C:5]2[Cl:22]

Participants

Conditions

Temperature: 0 °C

Procedure

6-Bromo-2-(2-fluoro-phenyl)-3H-quinazolin-4-one from Step C (1.5 g, 4.6 mmol) was suspended in chloroform in a 50 ml round bottomed flask equipped with magnetic stirrer. The flask was cooled to 0° C. and to it was added thionyl chloride (1.6 ml) drop wise followed by N,N-dimethyl formamide (0.01 ml) and the mixture heated to 80° C. for 4 hrs. The solvent was removed by evaporation in a rotary evaporator to leave a title compound as a solid (1.43 g, 90%). MS (ES) 338 (M+H)+

Workup

customequipped with magnetic stirrer
temperaturethe mixture heated to 80° C. for 4 hrs
customThe solvent was removed by evaporation in a rotary evaporator

Sources & evidence

ORD record: ord-905d585b6330437fbc29f1f5cb2bf0ab
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07189733B2

Reaction notes

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