Calcium Chloride → Benzenamine,4-[(imidazo[1,2-a]pyridin-3-ylmethyl)thio]-

HRID 856662Notes

Reaction equation

HRID 856662 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][C:12]2[N:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]3=[N:14][CH:13]=2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[Ca+2].[Cl-]>C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][C:12]2[N:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]3=[N:14][CH:13]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 5284359Calcium ChlorideHCID 229383933-(4-Nitrophenylthiomethyl)imidazo[1,2-a]pyridine

Product 1

HCID 22938675Benzenamine,4-[(imidazo[1,2-a]pyridin-3-ylmethyl)thio]-Yield 84.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(4-nitrophenylthiomethyl)imidazo[1,2-a]pyridine (1.5 g), reduced iron (1.47 g) and calcium chloride (0.29 g) in 15% hydrous ethanol (45 ml) was heated to reflux for 5 hours. After cooling to room temperature, and the precipitates were removed by filtration. After concentrating the filtrate, water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The precipitated crystals were collected by filtration. The crystals were washed with diisopropylether, to give 3-(4-aminophenylthiomethyl)imidazo[1,2-a]pyridine (1.13 g) as pale yellow crystals.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 hours
  3. customthe precipitates were removed by filtration
  4. concentrationAfter concentrating the filtrate, water
  5. additionwas added to the mixture
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. filtrationThe precipitated crystals were collected by filtration
  11. washThe crystals were washed with diisopropylether

Sources & evidence

ORD record
ord-72b251f80b084310822916fe9048e6c0
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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