Dimethylformamide → 4-Chloro-2-(2-fluoro-phenyl)-quinazoline

HRID 457712Notes

Reaction equation

HRID 457712 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:17][C:16](=O)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.S(Cl)([Cl:21])=O.CN(C)C=O>C(Cl)(Cl)Cl>[Cl:21][C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[N:17]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1355372902-(2-Fluorophenyl)quinazolin-4(1H)-one

Product 1

HCID 47382154-Chloro-2-(2-fluoro-phenyl)-quinazolineYield 73%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

2-(2-Fluoro-phenyl)-3H-quinazolin-4-one from Step B (0.86 g, 3.5 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 (1.2 ml) drop wise followed by N,N-dimethylformamide (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 (0.68 g, 73%). MS (ES) 259.1 (M+H)+

Workup

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

Sources & evidence

ORD record
ord-9304258f4a3e4083a278541306154611
Source dataset
uspto-grants-2007_03
Patent number
US07189733B2

Reaction notes

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