Morpholine → 4-(2-chloroquinazolin-4-yl)morpholine

HRID 1076358Notes

Reaction equation

HRID 1076358 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>C(O)C.O>[Cl:1][C:2]1[N:11]=[C:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 2528862,4-Dichloroquinazoline2×

Product 1

HCID 23384664-(2-chloroquinazolin-4-yl)morpholineYield 73.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Twenty grams of 2,4-dichloroquinazoline was suspended in 200 ml of ethanol. To this suspension was added 17.4 g of morpholine. A mildly exothermic reaction ensued with the concomitant dissolution of the suspended dichloroquinazoline. When the reaction subsided, after about 10 minutes, the mixture was heated at reflux for 15 minutes, and then was allowed to cool. The reaction mixture then was diluted with 800 ml of water. The solid which precipitated was collected by filtration and was washed with water. After drying, the solid was recrystallized from 1:2 benzene:hexane, to give 18.5 g of 2-chloro-4-morpholinoquinazoline; m.p. 103°-105°. The following analytical data were obtained:

Workup

  1. customA mildly exothermic reaction
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 15 minutes
  4. temperatureto cool
  5. customThe solid which precipitated
  6. filtrationwas collected by filtration
  7. washwas washed with water
  8. customAfter drying
  9. customthe solid was recrystallized from 1:2 benzene

Sources & evidence

ORD record
ord-6fbb3294371d4c2cbbb6eec100850c5e
Source dataset
uspto-grants-1976_05
Patent number
US03956495

Reaction notes

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