HCID 20212028, compound → HCID 20212024, compound

HRID 464379Notes

Reaction equation

HRID 464379 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:12]1[C:17]([C:18]([O:20]CC)=[O:19])=[C:16]([CH3:23])[CH:15]=[C:14]([CH3:24])[N:13]=1>Cl>[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:12]1[C:17]([C:18]([OH:20])=[O:19])=[C:16]([CH3:23])[CH:15]=[C:14]([CH3:24])[N:13]=1

Participants

3

Reactant 1

HCID 20212028HCID 20212028, compound

Product 1

HCID 20212024HCID 20212024, compoundYield 8.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Ethyl 2-[2-(5-methyl-4-imidazolylmethylthio)ethyl]amino-4,6-dimethylpyridine-3-carboxylate (2.45 g, 0.0070 moles) was hydrolysed by refluxing with an excess of conc. hydrochloric acid (20 ml) for 20 hours. The reaction mixture was next evaporated to dryness, dissolved in a little water and basified to ph7.5 using 2N sodium hydroxide solution. After evaporating off water, the residue was dissolved in ethanol and adsorbed onto silica gel, followed by chromatography on silica gel using chloroform/methanol (10:1). The crude product was recrystallised from water to give 2-[2-(5-methyl-4-imidazolylmethylthio)ethyl]amino-4,6-dimethyl pyridine-3-carboxylic acid (0.20 g) which sublimes with decomposition above 110°. NMR data:

Workup

  1. customThe reaction mixture was next evaporated to dryness
  2. dissolutiondissolved in a little water and basified to ph7.5
  3. customAfter evaporating off water
  4. dissolutionthe residue was dissolved in ethanol
  5. customThe crude product was recrystallised from water

Sources & evidence

ORD record
ord-8c05865000c9498886e032db05702203
Source dataset
uspto-grants-1985_10
Patent number
US04547512

Reaction notes

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