Phosphorus oxychloride → 4-(4-Chloro-2-quinazolinyl)-N,N-dimethylbenzenamine

HRID 717331Notes

Reaction equation

HRID 717331 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:18]=[C:17](O)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1.O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([N:2]([CH3:20])[CH3:1])=[CH:4][CH:5]=2)[N:18]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178482694HCID 178482694, compound

Product 1

HCID 201611744-(4-Chloro-2-quinazolinyl)-N,N-dimethylbenzenamine

Conditions

Temperature
140 °C

Procedure

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2-[4-(dimethylamino)phenyl]quinazolin-4-ol (2 g, 7.54 mmol, 1.00 equiv) in POCl3 (20 mL). The resulting solution was stirred for 5 h at 140° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was dissolved in 50 mL of dichloromethane. The resulting mixture was washed with 2×20 mL of saturation sodium bicarbonate solution and 1×20 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 2.0 g (93%) of 4-(4-chloroquinazolin-2-yl)-N,N-dimethylaniline as a red solid. MS (ESI) m/z 284 ([M+H]+).

Workup

  1. customInto a 100-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. dissolutionThe residue was dissolved in 50 mL of dichloromethane
  5. washThe resulting mixture was washed with 2×20 mL of saturation sodium bicarbonate solution and 1×20 mL of brine
  6. dry with materialThe mixture was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThis resulted in 2.0 g (93%) of 4-(4-chloroquinazolin-2-yl)-N,N-dimethylaniline as a red solid

Sources & evidence

ORD record
ord-71b07ce2d0f54ac0acf4062c29316224
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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