Sodium Carbonate → HCID 14302387, compound

HRID 1200251Notes

Reaction equation

HRID 1200251 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH2:11]Cl.[N+:13]([C:16]1[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=1)([O-:15])=[O:14].C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])[O-].[Na+].[Na+]>[I-].[K+].CC(C)=O>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH2:11][O:22][C:18]1[CH:17]=[C:16]([N+:13]([O-:15])=[O:14])[CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 10796Cesium carbonateHCID 111373-NitrophenolHCID 2480442-(Chloromethyl)-1-methylbenzimidazole

Product 1

HCID 14302387HCID 14302387, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

A mixture of 1-methyl-2-(chloromethyl)benzimidazole (9.8 g), 3-nitrophenol (7.5 g), cesium carbonate (17.6 g), sodium carbonate (5.7 g), potassium iodide (0.5 g) and acetone (250 ml) is heated at reflux overnight. The mixture is filtered and the resulting solution is partially concentrated. A crystalline solid forms which is filtered and dried, giving 10.8 g (70% yield) of title compound, m.p. 183°-185° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux overnight
  3. filtrationThe mixture is filtered
  4. concentrationthe resulting solution is partially concentrated
  5. filtrationA crystalline solid forms which is filtered
  6. customdried

Sources & evidence

ORD record
ord-19ca846b888f4097ac240f953711b1d3
Source dataset
uspto-grants-1990_02
Patent number
US04904786

Reaction notes

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