Calcium Chloride → HCID 43299418, compound

HRID 856708Notes

Reaction equation

HRID 856708 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[Ca+2].[Cl-]>C(O)C>[N:13]1([CH2:12][CH2:11][S:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

4

Reactant 2

HCID 5284359Calcium ChlorideHCID 23218986HCID 23218986, compound

Product 1

HCID 43299418HCID 43299418, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1-[2-[(4-nitrophenyl)sulfanyl]ethyl]imidazole (0.60 g) was added 85% ethanol solution (18 ml), and to this solution was added calcium chloride (0.13 g) and reduced iron (0.67 g), and the mixture was heated to reflux for 3 hours. After cooling to room temperature, the mixture was filtered with Celite, and washed with ethyl acetate. The solvent was removed under reduced pressure, and the obtained residue was dissolved in ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 4-[[2-(imidazol-1-yl)ethyl]sulfanyl]phenylamine (0.48 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. filtrationthe mixture was filtered with Celite
  4. washwashed with ethyl acetate
  5. customThe solvent was removed under reduced pressure
  6. dissolutionthe obtained residue was dissolved in ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was removed under reduced pressure
  10. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cb07217528d54b84ae5afb264d34435a
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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