Acetic Acid → 4-bromo-2-methyl-6-nitro-1H-benzo[d]imidazole

HRID 1622439Notes

Reaction equation

HRID 1622439 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([NH2:11])[C:3]=1[NH2:12].[C:13](O)(=O)[CH3:14]>>[Br:1][C:2]1[C:3]2[N:12]=[C:13]([CH3:14])[NH:11][C:4]=2[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 203480123-Bromo-5-nitrobenzene-1,2-diamine

Product 1

HCID 866878134-bromo-2-methyl-6-nitro-1H-benzo[d]imidazoleYield 56.6%

Procedure

A mixture of 3-bromo-5-nitrobenzene-1,2-diamine (90 g, 389 mmol) in acetic acid (800 mL) was stirred under reflux for 18 h. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=1/1) to give the product (56 g, 56.6%) as a brown solid; LC/MS: MS (ES+) m/e 256 [M+H]+; 1H NMR (300 MHz, DMSO-d6) δ ppm 2.60 (s, 3H), 8.20 (d, J=1.8 Hz, 3H), 8.34 (d, J=1.8 Hz, 2H), 13.25 (s, br, 1H).

Workup

  1. temperatureunder reflux for 18 h
  2. customThe solvent was removed in vacuo
  3. customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-9d893dcbf9fc41ed921e36f3dfd92431
Source dataset
uspto-grants-2014_07
Patent number
US08778937B2

Reaction notes

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