Dimethylformamide → 4-bromo-2-isopropyl-1-(2-methyl-3-(trifluoromethyl)benzyl)-6-nitro-1H-benzo[d]imidazole

HRID 1622490Notes

Reaction equation

HRID 1622490 reaction equation
CN(C=O)C.[Br:6][C:7]1[C:15]2[N:14]=[C:13]([CH:16]([CH3:18])[CH3:17])[NH:12][C:11]=2[CH:10]=[C:9]([N+:19]([O-:21])=[O:20])[CH:8]=1.Br[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[C:25]=1[CH3:34].C(=O)([O-])[O-].[K+].[K+]>O>[Br:6][C:7]1[C:15]2[N:14]=[C:13]([CH:16]([CH3:18])[CH3:17])[N:12]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:31])([F:32])[F:33])[C:25]=3[CH3:34])[C:11]=2[CH:10]=[C:9]([N+:19]([O-:21])=[O:20])[CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27756171-(Bromomethyl)-2-methyl-3-(trifluoromethyl)benzeneHCID 866878464-bromo-2-isopropyl-6-nitro-1H-benzo[d]imidazole

Product 1

HCID 866878474-bromo-2-isopropyl-1-(2-methyl-3-(trifluoromethyl)benzyl)-6-nitro-1H-benzo[d]imidazoleYield 108%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100 mL round bottomed flask containing DMF (50 mL) was added 4-bromo-2-isopropyl-6-nitro-1H-benzo[d]imidazole (4.1 g, 14.43 mmol), 1-(bromomethyl)-2-methyl-3-(trifluoromethyl)benzene (3.6 mL, 21.34 mmol) and potassium carbonate (5.98 g, 43.3 mmol). The resultant suspension was heated to 50° C. and after stirring for 30 minutes the mixture was allowed to cool to rt and diluted with 100 mL H2O. The mixture was stirred overnight and the next day a black filterable solid was isolated by filtration providing crude 4-bromo-2-isopropyl-1-(2-methyl-3-(trifluoromethyl)benzyl)-6-nitro-1H-benzo[d]imidazole (7.1 g, 15.56 mmol, 108% yield). MS (ES+) m/e: 455.1, 455.9 [M+H]+

Workup

  1. stirringThe mixture was stirred overnight
  2. customthe next day a black filterable solid was isolated by filtration

Sources & evidence

ORD record
ord-b737d785f7dd4848818ed2dff409037a
Source dataset
uspto-grants-2014_07
Patent number
US08778937B2

Reaction notes

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