Dimethylformamide → 4-Chloro-2-phenylquinazoline

HRID 1973870Notes

Reaction equation

HRID 1973870 reaction equation
[C:1]1([C:7]2[NH:16][C:15](=O)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:20])=O.CN(C)C=O>C(Cl)Cl>[Cl:20][C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:16]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1354004562-Phenyl-4(3H)-Quinazolinone

Product 1

HCID 809774-Chloro-2-phenylquinazoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 20.8 g of 2-phenylquinazolin-4(3H)-one and 195 ml of thionyl chloride was slowly added 6.85 g of dimethylformamide and the mixture was heated under reflux for 75 minutes. The mixture was poured into 1000 ml of ice and the ice allowed to melt. The precipitate was collected by filtration to give a tan solid, m.p. 135°. The still-moist solid was dissolved in methylene chloride, the solution was dried over magnesium sulfate and was filtered. The filtrate was evaporated to dryness and the residue recrystallized from hexane to give 10.45 g of 4-chloro-2-phenylquinazoline which melted at 127°-128.5°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 75 minutes
  3. filtrationThe precipitate was collected by filtration
  4. customto give a tan solid, m.p. 135°
  5. dry with materialthe solution was dried over magnesium sulfate
  6. filtrationwas filtered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue recrystallized from hexane

Sources & evidence

ORD record
ord-9939188f98b94effa06a371282d86730
Source dataset
uspto-grants-1976_12
Patent number
US03998951

Reaction notes

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