Nitrobenzene → HCID 9839420, compound

HRID 50881Notes

Reaction equation

HRID 50881 reaction equation
[CH:1]([C:9]1[NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[N:10]=1)=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:19]1[S:20][CH:21]=[CH:22][N:23]=1.C(=O)([O-])[O-].[K+].[K+].[N+](C1C=CC=CC=1)([O-])=O>C(OCC)(=O)C.[Cu]>[CH:1](/[C:9]1[N:10]([C:19]2[S:20][CH:21]=[CH:22][N:23]=2)[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1)=[CH:2]\[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 7416NitrobenzeneHCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 2429652-(2-Phenylethenyl)-1h-benzimidazole

Product 1

HCID 9839420HCID 9839420, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A stirred mixture of 2-styryl-1H-benzimidazole (220 mg, 1 mmol), 2-bromothiazole (328 mg, 2 mmol), potassium carbonate (138 mg, 1 mmol), copper bronze (20 mg) and nitrobenzene (10 ml) was heated to reflux under a nitrogen atmosphere for 7 h. The cooled reaction mixture was diluted with ethyl acetate (150 ml) and filtered through a pad of celite. The filtrate was washed consecutively with water (50 ml), and brine (50 ml), dried (magnesium sulfate) and concentrated to dryness. Column chromatography (silica gel, 100 g; n-hexane/ethyl acetate (9/1 to 3/1)) gave 199 mg of the titled compound as an orange oil, which was solidified on standing at room temperature. Recrystallization from isopropyl ether gave 117 mg (39%) of the titled compound as colorless crystals. MW: 303.39; mp: 99.0-99.5° C.; 1H-NMR (CDCl3) δ: 8.01 (1H. d, J=15.8 Hz), 7.91 (1H, d, J=3.7 Hz), 7.85-7.80 (1H, m), 7.69-7.64 (1H, m), 7.59-7.54 (2H, m), 7.51 (1H, d, J=3.7 Hz), 7.40 (1H, d, J=15.8 Hz), 7.42-7.29 (5H, m).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under a nitrogen atmosphere for 7 h
  3. customThe cooled reaction mixture
  4. filtrationfiltered through a pad of celite
  5. washThe filtrate was washed consecutively with water (50 ml), and brine (50 ml)
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a05508c089f742349ab9d629e98e4f04
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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