Potassium Carbonate → 6-bromo-2-(1-methylethyl)-1-(1-naphthalenylmethyl)-4-nitro-1H-benzimidazole

HRID 44482

Reaction equation

HRID 44482 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[C:5]2[N:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[NH:7][C:6]=2[CH:13]=1.Br[CH2:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[C:5]2[N:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[N:7]([CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21][CH:20]=3)[C:6]=2[CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1378441-(Bromomethyl)naphthaleneHCID 669767256-bromo-2-isopropyl-4-nitro-1H-benzo[d]imidazole

Product 1

HCID 669768966-bromo-2-(1-methylethyl)-1-(1-naphthalenylmethyl)-4-nitro-1H-benzimidazoleYield 102.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-bromo-2-isopropyl-4-nitro-1H-benzo[d]imidazole (4.7 g), 1-(bromomethyl)naphthalene (4.01 g) and K2CO3 (4.55 g) in DMF (150 mL) was stirred at 80° C. for 2 h. It was cooled to room temperature and filtered. The filtrate was then poured into water (1 L). It was then filtered to afford a solid that was washed with water and then dried in-vacuo to afford the crude product (7.2 g). LC-MS: m/e=425 [M+1]+

Workup

  1. temperatureIt was cooled to room temperature
  2. filtrationfiltered
  3. additionThe filtrate was then poured into water (1 L)
  4. filtrationIt was then filtered
  5. customto afford a solid
  6. washthat was washed with water
  7. customdried in-vacuo

Sources & evidence

ORD record
ord-652cf95ec8b94d8c811f7498dd9f7fb1
Source dataset
uspto-grants-2013_09
Patent number
US08541411B2

Linked notes

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