Butyl bromide → HCID 23318987, compound

HRID 1981564Notes

Reaction equation

HRID 1981564 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[C:18]2[NH:23][C:24](=[O:26])[CH2:25][N:17]2[CH2:16]3)[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Br[CH2:30][CH2:31][CH2:32][CH3:33]>CN(C)C=O>[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[C:18]2[N:23]([CH2:30][CH2:31][CH2:32][CH3:33])[C:24](=[O:26])[CH2:25][N:17]2[CH2:16]3)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 135668094HCID 135668094, compound

Product 1

HCID 23318987HCID 23318987, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 7-(6-(N-imidazolyl)hexyl)oxy-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one in dry dimethylformamide is added sodium hydride (1.05 equivalents). The mixture is stirred at 60° C. for 30 minutes to give a homogeneous solution. 1-bromobutane (1.1 equivalents) is added via a syringe after which the mixture is stirred at 60° C. for 2 hours. The solvent is evaporated and the residue taken up in ethyl acetate which is washed with saturated brine, dried and filtered. Evaporation of the solvent affords 7-(6-(N-imidazolyl)hexyl)oxy-1-butyl-1,2,3,5-tetrahydroimidazo[2,1-b]-quinazolin-2-one.

Workup

  1. customto give a homogeneous solution
  2. stirringis stirred at 60° C. for 2 hours
  3. customThe solvent is evaporated
  4. washis washed with saturated brine
  5. customdried
  6. filtrationfiltered
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-80212c01ffa8402f901c4051be0090c9
Source dataset
uspto-grants-1986_06
Patent number
US04593029

Reaction notes

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