Ethanol → HCID 69521322, compound

HRID 856788Notes

Reaction equation

HRID 856788 reaction equation
[CH3:1][C:2]1[N:7]2[C:8]([CH2:11][S:12][C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)=[CH:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[Cl-].[Ca+2].[Cl-].C(O)C>O>[CH3:1][C:2]1[N:7]2[C:8]([CH2:11][S:12][C:13]3[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=3)=[CH:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 5284359Calcium ChlorideHCID 69522241HCID 69522241, compound

Product 1

HCID 69521322HCID 69521322, compoundYield 103.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-methyl-3-[(4-nitrophenylthio) methyl]imidazo[1,2-a]pyridine (1.80 g), reduced iron (1.68 g) and calcium chloride (0.33 g) in 15% water-containing ethanol (54 ml) was heated to reflux for 24 hours. The insolubles were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was extracted with ethyl acetate, washed with saturated brine, and dried over magnesium sulfate. The solvent was concentrated under reduced pressure. The obtained residue was separated and purified by column chromatography (ethyl acetate:hexane 1:1→2:1), to give 4-[[(5-methylimidazo[1,2-a]pyridin-3-yl)methyl]thio]aniline (1.67 g) as yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. customThe insolubles were removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. extractionThe residue was extracted with ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe solvent was concentrated under reduced pressure
  9. customThe obtained residue was separated
  10. custompurified by column chromatography (ethyl acetate:hexane 1:1→2:1)

Sources & evidence

ORD record
ord-cb2e417a1fc744d5a0b795f48562ebd3
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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