Ethanol → HCID 21412358, compound

HRID 1076364Notes

Reaction equation

HRID 1076364 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:18]([NH2:21])[CH2:19][NH2:20].C(O)C.[OH-].[Na+]>O>[ClH:1].[ClH:1].[NH2:20][CH2:19][CH2:18][NH:21][C:2]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 3301EthylenediamineHCID 14798Sodium HydroxideHCID 23384664-(2-chloroquinazolin-4-yl)morpholine

Product 1

HCID 21412358HCID 21412358, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4 g of 2-chloro-4-morpholinoquinazoline, 5 ml of ethylenediamine, and 10 ml. of ethanol was heated at reflux overnight. The reaction mixture was diluted with 200 ml of water made alkaline with 15 ml of 50 percent aqueous sodium hydroxide solution, and extracted with one liter of ether. The ether extract was washed with water, dried over anhydrous sodium sulfate, filtered, and evaporated. The residue was dissolved in 500 ml of ether and treated with excess hydrogen chloride. The crude product was collected by filtration and recrystallized from the ether-ethanol, to give 1 g of 2-(2-aminoethylamino)-4-morpholinoquinazoline dihydrochloride; m.p. 292°-294° with decomposition. The following analytical data were obtained:

Workup

  1. temperatureat reflux overnight
  2. extractionextracted with one liter of ether
  3. extractionThe ether extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. dissolutionThe residue was dissolved in 500 ml of ether
  9. additiontreated with excess hydrogen chloride
  10. filtrationThe crude product was collected by filtration
  11. customrecrystallized from the ether-ethanol

Sources & evidence

ORD record
ord-c40679f9d4164faabf8d888f8b6bf4d4
Source dataset
uspto-grants-1976_05
Patent number
US03956495

Reaction notes

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