Acetic Acid → 4-{[bis(1-methyl-1H-imidazol-2-ylmethyl)amino]methyl}-benzoic Acid

HRID 348636Notes

Reaction equation

HRID 348636 reaction equation
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1CN.[CH3:13][N:14]1[CH:18]=[CH:17][N:16]=[C:15]1[CH:19]=O.[C:21]([BH3-])#[N:22].[Na+].[C:25](O)(=O)[CH3:26]>CO>[CH3:13][N:14]1[CH:18]=[CH:17][N:16]=[C:15]1[CH2:19][N:22]([CH2:21][C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:2])=[O:12])=[CH:9][CH:8]=1)[CH2:19][C:15]1[N:14]([CH3:13])[CH:25]=[CH:26][N:16]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 2760944Methyl 2-(aminomethyl)benzoateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 669418054-{[bis(1-methyl-1H-imidazol-2-ylmethyl)amino]methyl}-benzoic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Commercially available amino methylbenzoic acid methyl ester (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (278 mg) was dissolved in methanol (9 ml). Then, the solution was added with 1-methyl-2-imidazole carboxaldehyde (manufactured by Aldrich Corporation) (407 mg) and sodium cyanoborohydride (317 mg), and then adjusted to about pH 5 with acetic acid, followed by stirring at room temperature for 3 days. After completion of the reaction, the solvent was distilled off and the residue was then dissolved in chloroform, followed by washing with a 1 mol/l sodium hydroxide solution. The solution was dried with anhydrous sodium sulfate, and the solvent was distilled off. Subsequently, the residue was dissolved in methanol (6.0 ml) and then added with 1 mol/l sodium hydroxide, followed by stirring at room temperature for 6 hours. After completion of the reaction, 1 mol/l hydrochloric acid (6.0 ml) was added and the solvent was distilled off. After that, ethanol was added to remove insoluble matter, the solvent was distilled off, and the residue was then dried, thereby obtaining the subject compound (519 mg) as a pale-yellow foamy substance.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionthe residue was then dissolved in chloroform
  4. washby washing with a 1 mol/l sodium hydroxide solution
  5. dry with materialThe solution was dried with anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. dissolutionSubsequently, the residue was dissolved in methanol (6.0 ml)
  8. additionadded with 1 mol/l sodium hydroxide
  9. stirringby stirring at room temperature for 6 hours
  10. customAfter completion of the reaction, 1 mol/l hydrochloric acid (6.0 ml)
  11. additionwas added
  12. distillationthe solvent was distilled off
  13. additionAfter that, ethanol was added
  14. customto remove insoluble matter
  15. distillationthe solvent was distilled off
  16. customthe residue was then dried

Sources & evidence

ORD record
ord-7e25fbcd556647af89095f19b40122f2
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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