Thionyl Chloride → 4-chloro-2-(4-chlorophenyl)quinazoline

HRID 1973872Notes

Reaction equation

HRID 1973872 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:17][C:16](=O)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:21])=O>CN(C)C=O>[Cl:21][C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:17]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1354042472-(4-Chlorophenyl)quinazolin-4-ol

Product 1

HCID 8182744-chloro-2-(4-chlorophenyl)quinazoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 15.8 g of 2-(4-chlorophenyl)quinazolin-4(3H)-one and 115 ml of thionyl chloride was added dropwise 4.5 g of dimethylformamide and the mixture was treated as described in Example I to obtain a yellow solid which was recrystallized from cyclohexane to give 13.6 g of light yellow 4-chloro-2-(4-chlorophenyl)quinazoline, m.p. 166°-167°; ir and nmr spectra were consistent with the assigned structure.

Workup

  1. additionthe mixture was treated
  2. customto obtain a yellow solid which
  3. customwas recrystallized from cyclohexane

Sources & evidence

ORD record
ord-a79cdb8d4eae4ee58c66051fdf12f9bc
Source dataset
uspto-grants-1976_12
Patent number
US03998951

Reaction notes

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