Sodium Chloride → HCID 16045795, compound

HRID 1410180Notes

Reaction equation

HRID 1410180 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([NH2:15])[NH:13][CH:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:16][O:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20]Cl.C([O-])([O-])=O.[Cs+].[Cs+].[Cl-].[Na+]>CN(C)C=O>[CH3:16][O:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20][N:13]1[CH:14]=[C:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[N:11]=[C:12]1[NH2:15]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 10796Cesium carbonateHCID 814952-(Chloromethyl)anisoleHCID 178508304HCID 178508304, compound

Product 1

HCID 16045795HCID 16045795, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(4-nitrophenyl)-1H-imidazole-2-ylamine (0.9 g, 4.4 mmol), 2-methoxybenzyl chloride (0.69 g, 4.4 mmol), and Cs2CO3 (1.6 g, 4.9 mmol) in dimethylformamide was stirred for 18 hr at room temperature. The batch was combined with 50% sodium chloride solution and extracted with ethyl acetate. The organic phase was washed several times with water and saturated sodium chloride solution and concentrated, and the residue was purified on silica gel using methylene chloride/methanol 50:1 (100 mg of a red solid).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed several times with water and saturated sodium chloride solution
  3. concentrationconcentrated
  4. customthe residue was purified on silica gel

Sources & evidence

ORD record
ord-f88f296bf56a4da2be9d7598686d8c95
Source dataset
uspto-grants-2014_12
Patent number
US08921406B2

Reaction notes

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