Potassium Carbonate → 4-[1-(4-chloro-3-nitrophenacyl)-1H-benzimidazol-2-yl]-furazan-3-ylamine

HRID 132013Notes

Reaction equation

HRID 132013 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:15])=[N:12][O:13][N:14]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:22][C:23]1[CH:32]=[CH:31][C:26]([C:27](=[O:30])[CH2:28]Br)=[CH:25][C:24]=1[N+:33]([O-:35])=[O:34]>CN(C=O)C.C(OCC)(=O)C>[Cl:22][C:23]1[CH:32]=[CH:31][C:26]([C:27](=[O:30])[CH2:28][N:3]2[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]=[C:2]2[C:10]2[C:11]([NH2:15])=[N:12][O:13][N:14]=2)=[CH:25][C:24]=1[N+:33]([O-:35])=[O:34]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 7385314-(1H-benzimidazol-2-yl)-1,2,5-oxadiazol-3-amineHCID 27783302-Bromo-1-(4-chloro-3-nitrophenyl)ethan-1-one

Product 1

HCID 674590044-[1-(4-chloro-3-nitrophenacyl)-1H-benzimidazol-2-yl]-furazan-3-ylamine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 4-(1H-benzimidazol-2-yl)-furazan-3-ylamine (0.228 g, 1.14 mmol), potassium carbonate (0.40 g, 2.85 mmol) and 4-chloro-3-nitrophenacyl bromide (0.35 g, 1.25 mmol) in DMF (5 ml) is stirred at room temperature for 16 hours. The reaction mixture is diluted with ethyl acetate, washed with water and dried over sodium sulphate. Filtration of the sodium sulphate, concentration of the filtrate under reduced pressure and chromatography of the residue on silicagel using hexane-ethyl acetate as eluent gives the title compound as a solid, m.p. 198-200° C. (This compound is also listed as Example 66 in Table 1.)

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulphate
  3. filtrationFiltration of the sodium sulphate, concentration of the filtrate under reduced pressure and chromatography of the residue on silicagel

Sources & evidence

ORD record
ord-4e17a1d986e0494ebc44c1a311ec3aba
Source dataset
uspto-grants-2008_06
Patent number
US07385061B2

Reaction notes

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