Phosphorus oxychloride → 4-chloro-N,N-dimethylquinazolin-6-amine

HRID 596609Notes

Reaction equation

HRID 596609 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][NH:7][C:6]2=O.P(Cl)(Cl)([Cl:17])=O>CCOCC>[CH3:1][N:2]([CH3:14])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][N:7]=[C:6]2[Cl:17]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1358112116-(Dimethylamino)-3,4-dihydroquinazolin-4-one

Product 1

HCID 233667574-chloro-N,N-dimethylquinazolin-6-amine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 12.4 g. of 6-dimethylamino-quinazolin-4(3H)-one and 50 ml. of phosphorus oxychloride is refluxed under nitrogen for 10 minutes, cooled to room temperature, 150 ml. of ether added, the crystals recovered by filtering, washed with ether and dried. The solids are added to 500 ml. of ice-water, concentrated ammonia is added to neutralize the solution which is extracted with 1.0 liter of chloroform. The chloroform extract is dried and filtered through 300 ml. of silica gel using chloroform as an eluant. Evaporation of the eluant yields 6-dimethylamino-4-chloroquinazoline, m.p. 126°-127.5° C.

Workup

  1. additionA mixture of 12.4 g
  2. customthe crystals recovered
  3. filtrationby filtering
  4. washwashed with ether
  5. customdried
  6. additionThe solids are added to 500 ml
  7. additionof ice-water, concentrated ammonia is added
  8. extractionis extracted with 1.0 liter of chloroform
  9. extractionThe chloroform extract
  10. customis dried
  11. filtrationfiltered through 300 ml
  12. customEvaporation of the eluant

Sources & evidence

ORD record
ord-4dc27b9c24534498909634ddcf26ab2e
Source dataset
uspto-grants-1977_03
Patent number
US04011323

Reaction notes

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