Phosphorus oxychloride → 4-Chloro-2,8-dimethyl-8-phenyl-5,6,7,8-tetrahydroquinazoline

HRID 1354096Notes

Reaction equation

HRID 1354096 reaction equation
[CH3:1][C:2]1[N:11]=[C:10](O)[C:9]2[CH2:8][CH2:7][CH2:6][C:5]([CH3:19])([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]=2[N:3]=1.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:10]1[C:9]2[CH2:8][CH2:7][CH2:6][C:5]([CH3:19])([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]=2[N:3]=[C:2]([CH3:1])[N:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178433414HCID 178433414, compound

Product 1

HCID 211043804-Chloro-2,8-dimethyl-8-phenyl-5,6,7,8-tetrahydroquinazoline

Procedure

A mixture of 2,8-dimethyl-8-phenyl-5,6,7,8-tetrahydro-quinazolin-4-ol (4 g, 16 mmol) and 25 mL of phosphorous oxychloride was heated under reflux for 2 hours, concentrated under reduced pressure and ice, water and dichloromethane were added. The mixture was basified with aqueous sodium carbonate and the organic layer was dried (sodium sulfate) and evaporated to afford 4.4 g of 4-chloro-2,8-dimethyl-8-phenyl-5,6,7,8-tetrahydroquinazoline as an oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. concentrationconcentrated under reduced pressure and ice, water and dichloromethane
  4. additionwere added
  5. dry with materialthe organic layer was dried (sodium sulfate)
  6. customevaporated

Sources & evidence

ORD record
ord-b398dc5a99ab4f8e82ea04d69a9a9470
Source dataset
uspto-grants-2007_05
Patent number
US07223767B2

Reaction notes

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