Thionyl Chloride → 4-Chloro-6-methyl-2-phenylquinazoline

HRID 1973871Notes

Reaction equation

HRID 1973871 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH:6][C:5]2=O.S(Cl)([Cl:21])=O>CN(C)C=O>[Cl:21][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH3:1])[CH:3]=2)[N:8]=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1356776016-Methyl-2-phenyl-4(3H)-quinazolinone

Product 1

HCID 214906444-Chloro-6-methyl-2-phenylquinazoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred slurry of 2.1 g of 6-methyl-2-phenylquinazolin-4(3H)-one and 35 ml of thionyl chloride was added dropwise 1.3 g of dimethylformamide. The mixture was maintained at reflux temperature for 90 minutes. The mixture was concentrated under reduced pressure, the residual solid was mixed with crushed ice and the washed solid collected. Two recrystallizations from petroleum ether (60°-110° fraction) gave 1.5 g of 4-chloro-6-methyl-2-phenylquinazoline, m.p. 111°-113°.

Workup

  1. temperatureThe mixture was maintained
  2. temperatureat reflux temperature for 90 minutes
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionthe residual solid was mixed with crushed ice
  5. customthe washed solid collected
  6. customTwo recrystallizations from petroleum ether (60°-110° fraction)

Sources & evidence

ORD record
ord-a8209c96ebd442b0b2a9268207697c9f
Source dataset
uspto-grants-1976_12
Patent number
US03998951

Reaction notes

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