Dimethylformamide → 4-Chloro-2-(3-nitrophenyl)quinazoline

HRID 61533Notes

Reaction equation

HRID 61533 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[NH:19][C:18](=O)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].CN(C=O)C.S(Cl)([Cl:28])=O>>[Cl:28][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[C:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:19]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1355026292-(3-nitrophenyl)quinazolin-4(3H)-one

Product 1

HCID 593619944-Chloro-2-(3-nitrophenyl)quinazoline

Procedure

To a suspension of 2-(3-nitrophenyl)quinazolin-4(3H)-one (5.7 g, 21.32 mmole) in thionyl chloride (70 mL) was added of DMF (2 mL). The reaction mixture was refluxed for 4.5 h. The reaction was then concentrated in vacuo and residue suspended in a mixture of CH2Cl2 (400 mL) and CHCl3 (500 mL). The organic layer was washed with water, saturated NaHCO3, water, brine, dried with Na2SO4 and concentrated in vacuo. The residue was dried under high vacuum to afford 4-chloro-2-(3-nitrophenyl)quinazoline as an off-white solid. (6.0 g, mmol, 97%).

Workup

  1. temperatureThe reaction mixture was refluxed for 4.5 h
  2. concentrationThe reaction was then concentrated in vacuo and residue
  3. additionsuspended in a mixture of CH2Cl2 (400 mL) and CHCl3 (500 mL)
  4. washThe organic layer was washed with water, saturated NaHCO3, water, brine
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-494f0a9da22a45f68fa51f096480811c
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Reaction notes

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