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

HRID 1973869Notes

Reaction equation

HRID 1973869 reaction equation
[CH3:1][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]([CH3:1])=[CH:3][CH:4]=2)[N:17]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1354521092-(4-Methylphenyl)quinazolin-4(3H)-one

Product 1

HCID 7320184-chloro-2-(4-methylphenyl)quinazoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 7 g of 2-(4-methylphenyl)quinazolin-4(3H)-one and 50 ml of thionyl chloride was slowly added 2.16 g of dimethylformamide and the mixture was heated under reflux for 75 minutes. The mixture was poured into 250 ml of ice and the ice allowed to melt. The precipitate was collected to give 6.7 g of 4-chloro-2-(4-methylphenyl)quinazoline which melted at 113°-115° after recrystallization from petroleum ether (30°-60° fraction); ir and nmr spectra were consistent with the assigned structure. Calcd. for C15H11ClN2 : C, 70.73; H, 4.35; N, 11.00. Found: C, 70.92; H, 4.39; N, 11.09.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 75 minutes
  3. customThe precipitate was collected

Sources & evidence

ORD record
ord-040e64e212574f88bc51a5fcea5d4a52
Source dataset
uspto-grants-1976_12
Patent number
US03998951

Reaction notes

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