Allyl bromide → HCID 13035731, compound
Reaction equation
[O:1]=[C:2]1[N:11]2[CH2:12][CH2:13][N:14]=[C:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[NH:3]1.[H-].[Na+].[CH3:17][CH2:18][CH2:19]CCC.C(Br)C=C>CC(N(C)C)=O>[O:1]=[C:2]1[N:11]2[CH2:12][CH2:13][N:14]=[C:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]1[CH2:19][CH:18]=[CH2:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
6.9 g (0.037 mol) of 5-oxo-2,3,5,6-tetrahydroimidazo-[1,2-c]-quinazoline in 60 ml of absolute dimethylacetamide were added to 1.75 g (0.058 mol) of an 80% strength suspension of NaH in oil (Schuchardt), after the suspension had been thoroughly stirred twice with 20 ml of n-hexane in each case and the solvent had been decanted, and the mixture was heated to 80° C. for 1 hour. During this process, a clear solution was gradually formed. The solution was cooled, and 4.6 ml (0.053 mol) of allyl bromide were added dropwise. The mixture was then heated to 100° C. for 4 hours. It was concentrated in a rotary evaporator to one third of its volume and was poured onto ice-water. The precipitated product was filtered off under suction and was recrystallised from methanol/water.
Workup
- customthe solvent had been decanted
- customDuring this process, a clear solution was gradually formed
- temperatureThe solution was cooled
- temperatureThe mixture was then heated to 100° C. for 4 hours
- concentrationIt was concentrated in a rotary evaporator to one third of its volume
- additionwas poured onto ice-water
- filtrationThe precipitated product was filtered off under suction
- customwas recrystallised from methanol/water
Sources & evidence
- ORD record
- ord-a97165cfadea437bab4000e7c24131c5
- Source dataset
- uspto-grants-1986_04
- Patent number
- US04585772
Reaction notes
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