Potassium Carbonate → HCID 11165682, compound

HRID 553338Notes

Reaction equation

HRID 553338 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]([NH:15][CH2:16][CH2:17][C:18]#[N:19])=[N:12][O:13][N:14]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:26][C:27]1[CH:36]=[CH:35][C:30]([C:31](=[O:34])[CH2:32]Br)=[CH:29][CH:28]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:26][C:27]1[CH:36]=[CH:35][C:30]([C:31](=[O:34])[CH2:32][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]([NH:15][CH2:16][CH2:17][C:18]#[N:19])=[N:12][O:13][N:14]=2)=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 68303p-Chlorophenacyl bromideHCID 1363893133-[4-(1H-Benzoimidazol-2-yl)-furazan-3-ylamino]-propionitrile

Product 1

HCID 11165682HCID 11165682, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 4-(1H-benzimidazol-2-yl)-furazan-3-yl-N-(2-cyanoethyl)-amine (0.10 g, 0.39 mmol), potassium carbonate (0.08 g, 0.58 mmol) and 4-chlorophenacyl bromide (0.11 g, 0.47 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 yellowish solid, m.p. 191-192° C.

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-18f14deab7bd4f55833e5a6152a7b1fa
Source dataset
uspto-grants-2011_11
Patent number
USRE042890E1

Reaction notes

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