Water → 2-(5-methyl-1-triphenylmethyl-1H-imidazol-4-yl)methyl-1,2-dihydro-imidazo[1,5-a]indol-3-one

HRID 363448Notes

Reaction equation

HRID 363448 reaction equation
[CH2:1]1[C:5]2=[CH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[N:4]2[C:3](=[O:13])[NH:2]1.[H-].[Na+].Cl[CH2:17][C:18]1[N:19]=[CH:20][N:21]([C:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]=1[CH3:23].O>CN(C)C=O>[CH3:23][C:22]1[N:21]([C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:20]=[N:19][C:18]=1[CH2:17][N:2]1[CH2:1][C:5]2=[CH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[N:4]2[C:3]1=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 110469654-(Chloromethyl)-5-methyl-1-trityl-1H-imidazoleHCID 700781451,2-Dihydro-imidazo[1,5-a]indol-3-one

Product 1

HCID 701026952-(5-methyl-1-triphenylmethyl-1H-imidazol-4-yl)methyl-1,2-dihydro-imidazo[1,5-a]indol-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 1,2-dihydro-imidazo[1,5-a]indol-3-one (3 g; 0.0174 moles) in 50 ml of anhydrous dimethylformamide kept under nitrogen atmosphere, 50% NaH (0.84 g; 0.0174 moles) is added. The solution is stirred for 1 hour at 60° C.; then, at room temperature, 4-chloromethyl-5-methyl-1-triphenylmethyl-1H-imidazole (6.5 g; 0.0174 moles) is added. The reaction mixture is stirred for 6 hours at 70° C., then cooled, poured into water and extracted with methylene chloride.

Workup

  1. stirringThe reaction mixture is stirred for 6 hours at 70° C.
  2. temperaturecooled
  3. extractionextracted with methylene chloride

Sources & evidence

ORD record
ord-143da9069d4f4435bf0df853114024bd
Source dataset
uspto-grants-1999_02
Patent number
US05874457

Reaction notes

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