HCID 4985365, compound → HCID 28412776, compound

HRID 856671Notes

Reaction equation

HRID 856671 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][S:9][C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[Ca+2].[Cl-]>C(O)C>[N:11]1[CH:12]=[CH:13][CH:14]=[N:15][C:10]=1[S:9][CH2:8][C:7]1[CH:16]=[CH:17][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4985365HCID 4985365, compoundHCID 5284359Calcium Chloride

Product 1

HCID 28412776HCID 28412776, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2-[(4-nitrobenzyl)sulfanyl]pyrimidine (8.0 g) was added 85% ethanol solution (160 ml), and then, calcium chloride (1.8 g) and reduced iron (9.0 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 organic layer was washed with water and 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-pyrimidinylsulfanyl)methyl]aniline (2.5 g).

Workup

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

Sources & evidence

ORD record
ord-4da2969aa4ad491f9ef4982d1fe87e58
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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