Potassium Carbonate → HCID 67460362, compound

HRID 132005Notes

Reaction equation

HRID 132005 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]([O:20][CH3:21])=[O:19])=[N:12][O:13][N:14]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:28][C:29]1[CH:38]=[CH:37][C:32]([C:33](=[O:36])[CH2:34]Br)=[CH:31][CH:30]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:28][C:29]1[CH:38]=[CH:37][C:32]([C:33](=[O:36])[CH2:34][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]([O:20][CH3:21])=[O:19])=[N:12][O:13][N:14]=2)=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 68303p-Chlorophenacyl bromideHCID 136413274HCID 136413274, compound

Product 1

HCID 67460362HCID 67460362, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 4-(1H-benzimidazol-2-yl)-furazan-3-yl-N-(2-methoxycarbonylethyl)-amine (0.052 g, 0.181 mmol), potassium carbonate (0.062 g, 0.452 mmol) and 4-chlorophenacyl bromide (0.047 g, 0.199 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 hygroscopic solid of undefined melting point. 1H-NMR (400 MHz, d6-DMSO): 8.14 (d, 2H); 7.87 (m, 2H); 7.41 (m, 2H); 7.32 (d, 2H); 7.29 (t, 1H); 6.37 (s, 2H); 3.63 (m, 2H); 3.61 (s, 3H); 2.76 (t, 2H).

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-10ac0b16cff54aa78cab26c9cac3dfb4
Source dataset
uspto-grants-2008_06
Patent number
US07385061B2

Reaction notes

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