Diethylamine → 9-Benzyl-2-diethylaminomethyl-3-ethoxycarbonylimidazo[1,2-a]benzimidazole

HRID 54698Notes

Reaction equation

HRID 54698 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[CH2:6]([N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]2[C:22]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:23]([CH2:25]Br)[N:24]=[C:14]12)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1C=CC=CC=1>[CH2:6]([N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]2[C:22]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:23]([CH2:25][N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[N:24]=[C:14]12)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 46163439-Benzyl-2-bromomethyl-3-ethoxycarbonylimidazo[1,2-a]benzimidazole

Product 1

HCID 199596929-Benzyl-2-diethylaminomethyl-3-ethoxycarbonylimidazo[1,2-a]benzimidazoleYield 96%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Add 1.04 ml (10 mmol) of diethylamine to a hot solution of 9-benzyl-2-bromomethyl-3-ethoxycarbonylimidazo[1,2-a]benzimidazole (2.01 g, 5 mmol), prepared as described for the alkylated analogues in Khim. Farm. ZH 88, 22 (7), 815-9, in 20 ml of benzene. Heat at reflux for one hour, cool. Remove the resulting precipitate, evaporate the benzene, and the residue is recrystallised by hexane to yield the title compound.

Workup

  1. customprepared
  2. temperatureHeat
  3. temperatureat reflux for one hour
  4. temperaturecool
  5. customRemove the resulting precipitate
  6. customevaporate the benzene
  7. customthe residue is recrystallised by hexane

Sources & evidence

ORD record
ord-c998c6eeba634e6ba5c4ba58f411b129
Source dataset
uspto-grants-1997_04
Patent number
US05623073

Reaction notes

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