Hydrochloric Acid → HCID 69522816, compound

HRID 856789Notes

Reaction equation

HRID 856789 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:11][C:12]1[CH:13]=[CH:14][C:15]2[N:16]([C:18]([CH2:21]O)=[CH:19][N:20]=2)[CH:17]=1.Cl.[OH-].[Na+]>C(O)(=O)C>[CH3:11][C:12]1[CH:13]=[CH:14][C:15]2[N:16]([C:18]([CH2:21][S:10][C:7]3[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)=[CH:19][N:20]=2)[CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 158094-NitrobenzenethiolHCID 10630828HCID 10630828, compound

Product 1

HCID 69522816HCID 69522816, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-nitrothiophenol (2.87 g), 6-methylimidazo[1,2-a]pyridin-3-ylmethanol (3.0 g), concentrated hydrochloric acid (60 ml) and acetic acid (60 ml) was stirred for 5 days at 100° C. The mixture was neutralized with 12N sodium hydroxide at 0° C., and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was separated and purified by column chromatography (basic silica gel, ethyl acetate:hexane 2:1→4:1), to give 6-methyl-3-[[(4-nitrophenyl)thio]methyl]imidazo[1,2-a]pyridine (4.48 g) as pale yellow crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was separated
  6. custompurified by column chromatography (basic silica gel, ethyl acetate:hexane 2:1→4:1)

Sources & evidence

ORD record
ord-40ca0afd58cb44c48591a3d50d112499
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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