Ethanol → HCID 69521797, compound

HRID 856790Notes

Reaction equation

HRID 856790 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([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]=2)[CH:7]=1.[Cl-].[Ca+2].[Cl-].C(O)C>O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][S:12][C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=3)=[CH:9][N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 5284359Calcium ChlorideHCID 69522816HCID 69522816, compound

Product 1

HCID 69521797HCID 69521797, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-methyl-3-[[(4-nitrophenyl)thio]methyl]imidazo[1,2-a]pyridine (3.0 g), reduced iron (2.80 g) and calcium chloride (0.56 g) in 15% water-containing ethanol (150 ml) was heated to reflux for 20 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, and the obtained residue was separated and purified by column chromatography (ethyl acetate:hexane 1:1→2:1), to give 4-[[(6-methylimidazo[1,2-a]pyridin-3-yl)methyl]thio]aniline (2.38 g) as pale yellow crystals.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 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-22cbb4a86cc847978a6b282a162c8f3d
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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