Dimethylformamide → HCID 86715748, compound

HRID 627619Notes

Reaction equation

HRID 627619 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]2[C:3]=1[C:4](O)=[N:5][CH:6]=[N:7]2.S(Cl)([Cl:17])=O.CN(C)C=O>>[Cl:17][C:4]1[C:3]2[C:8](=[CH:9][C:10]([O:12][CH3:13])=[CH:11][C:2]=2[F:1])[N:7]=[CH:6][N:5]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178492907HCID 178492907, compound

Product 1

HCID 86715748HCID 86715748, compoundYield 94.9%

Conditions

Temperature
80 °C

Procedure

To a suspension of 5-fluoro-7-methoxyquinazolin-4-ol (0.125 g, 0.644 mmol) in thionyl chloride (1.410 mL, 19.31 mmol) was added N,N-dimethylformamide (0.028 mL, 0.361 mmol). The reaction was stirred at 80° C. for 6 hours and concentrated in vacuo. The residue was suspended in saturated aqueous sodium bicarbonate and extracted with dichloromethane. The organic layer was concentrated in vacuo to generate the title compound (0.13 g, 0.611 mmol) as a yellow solid. LC/MS (ESI+) m/z=213 (M+H).

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with dichloromethane
  3. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-164039db1ba141a8ae8b6ee98ebd9182
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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