Water → HCID 14153048, compound

HRID 1639136Notes

Reaction equation

HRID 1639136 reaction equation
[CH:1]([NH:3][CH2:4][C:5]([C:8]1[CH:23]=[CH:22][C:11]2[N:12]=[C:13]([C:15]3[CH:16]=[N:17][C:18]([OH:21])=[CH:19][CH:20]=3)[NH:14][C:10]=2[CH:9]=1)([CH3:7])[CH3:6])=[O:2].O.[OH-].[K+].[CH3:27]I>C(O)C>[CH:1]([NH:3][CH2:4][C:5]([C:8]1[CH:23]=[CH:22][C:11]2[N:12]=[C:13]([C:15]3[CH:16]=[N:17][C:18]([O:21][CH3:27])=[CH:19][CH:20]=3)[NH:14][C:10]=2[CH:9]=1)([CH3:7])[CH3:6])=[O:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 178449280HCID 178449280, compound

Product 1

HCID 14153048HCID 14153048, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3.5 g. of the 5-(2-formylaminomethylprop-2-yl)-2-(6-hydroxypyridin-3-yl)-benzimidazole (prepared in Example 4d) in 20 ml. water and 13.6 ml. 1N potassium hydroxide solution in ethanol is added 0.85 ml. methyl iodide, while cooling with water. After 24 hours, it is filtered off with suction and purified by column chromatography (silica gel, elution agent dichloromethane:methanolic ammonia=20:1 v/v). Appropriate fractions are combined, the solvent is removed in a vacuum and the residue is digested with ethanol/water. After filtering off with suction, there are obtained 2.2 g. (57% of theory) of the title compound which, per mole, still contains 0.75 mole of water, as colourless crystals which, in the air, become reddish coloured; m.p. 217°-221° C.

Workup

  1. filtrationit is filtered off with suction
  2. custompurified by column chromatography (silica gel, elution agent dichloromethane:methanolic ammonia=20:1 v/v)
  3. customthe solvent is removed in a vacuum
  4. filtrationAfter filtering off with suction, there
  5. customare obtained 2.2 g

Sources & evidence

ORD record
ord-e87fe49076904a5db7fcb126dd923e80
Source dataset
uspto-grants-1989_11
Patent number
US04882342

Reaction notes

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