N,N-Diethylethylenediamine → 1,2-Ethanediamine, N2-(2-chloro-4-quinazolinyl)-N1,N1-diethyl-, hydrochloride (1:2)
Reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].[Cl:9][C:10]1[N:19]=[C:18](Cl)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1>O1CCCC1>[ClH:9].[ClH:9].[Cl:9][C:10]1[N:19]=[C:18]([NH:6][CH2:5][CH2:4][N:3]([CH2:7][CH3:8])[CH2:1][CH3:2])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1Participants
Procedure
To a solution of 43.2 g of 2-diethylaminoethylamine (N,N-diethylethylenediamine) in 400 ml of tetrahydrofuran was added 54 g of 2,4-dichloroquinazoline. The mixture was stirred at ambient temperature overnight. The reaction mixture was evaporated almost to dryness and the residue was suspended in water. The aqueous medium was made alkaline with dilute sodium hydroxide and was extracted several times with ether. The combined ether extracts were washed with water, dried over anhydrous sodium sulfate, and filtered. The filtrate was saturated with anhydrous hydrogen chloride. The solid which precipitated was isolated by filtration and then was recrystallized from ethanol and ether, giving 53.8 g of 2-chloro-4-(2-diethylaminoethylamino)quinazoline dihydrochloride which decomposed at 152°. The following analytical data were obtained:
Workup
- customThe reaction mixture was evaporated almost to dryness
- extractionwas extracted several times with ether
- washThe combined ether extracts were washed with water
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- customThe solid which precipitated
- customwas isolated by filtration
- customwas recrystallized from ethanol and ether
Sources & evidence
- ORD record
- ord-b69b91fa6f2e44aa9b71307ca6f770a6
- Source dataset
- uspto-grants-1977_09
- Patent number
- US04048312
Reaction notes
Loading…