Benzyl Bromide → 6-bromo-2-methyl-4-nitro-1-(phenylmethyl)-1H-benzimidazole

HRID 539216Notes

Reaction equation

HRID 539216 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]2[N:9]=[C:8]([CH3:10])[NH:7][C:6]=2[CH:11]=1.BrC1NC2C=CC=CC=2N=1.Br[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]2[N:9]=[C:8]([CH3:10])[N:7]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:6]=2[CH:11]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27762812-BromobenzimidazoleHCID 669767706-Bromo-2-methyl-4-nitro-1H-benzo[d]imidazole

Product 1

HCID 669765686-bromo-2-methyl-4-nitro-1-(phenylmethyl)-1H-benzimidazoleYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-bromo-2-methyl-4-nitro-1H-benzo[d]imidazole, prepared as described in Example 1 (22 g), (bromomethyl)benzene (15 g) and K2CO3 (35 g) in DMF (250 mL) was stirred at 60° C. for 2 h. The reaction mixture was cooled to room temperature and filtered. The filtrate was then poured into water. It was then filtered to afford a solid and the solid was washed with water and then dried in-vacuo to afford the desired product (28 g, 93%). 1H NMR (300 MHz, DMSO-d6): δ ppm 2.60 (s, 3H), 5.62 (s, 2H), 7.12-7.15 (m, 2H), 7.29-7.39 (m, 3H), 8.12 (d, 1H, J=1.8 Hz), 8.32 (d, 1H, J=1.8 Hz); LC-MS: m/e=346 [M+1]+.

Workup

  1. customprepared
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. additionThe filtrate was then poured into water
  5. filtrationIt was then filtered
  6. customto afford a solid
  7. washthe solid was washed with water
  8. customdried in-vacuo

Sources & evidence

ORD record
ord-6cb5c12f5246484586a476e0ded38f35
Source dataset
uspto-grants-2014_10
Patent number
US08865912B2

Reaction notes

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