Ethanol → HCID 18404651, compound

HRID 1017990Notes

Reaction equation

HRID 1017990 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([O:13][CH3:14])=[S:12])=[N:8][CH:9]=1)([O-])=O.[Cl-].[NH4+].C(O)C>[Fe].O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([O:13][CH3:14])=[S:12])=[N:8][CH:9]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 18404587HCID 18404587, compound

Product 1

HCID 18404651HCID 18404651, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of methyl 5-nitro-(pyrid-2-yl)-thioacetate (6.3 g, Reference Example 2) iron powder (12 g), ammonium chloride (1 g), ethanol (150 ml) and water (150 ml) was heated at reflux for 2 hours. The reaction mixture was cooled and then filtered through a pad of diatomaceous earth. The filtrate was evaporated and the residue was subjected to flash chromatography on silica gel eluting with a mixture of ethyl acetate and pentane (1:1, v/v) to give the title compound as a yellow oil (3.0 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through a pad of diatomaceous earth
  5. customThe filtrate was evaporated
  6. additionthe residue was subjected to flash chromatography on silica gel eluting with a mixture of ethyl acetate and pentane (1:1

Sources & evidence

ORD record
ord-23457fd5163d4c6f8e3387573f5d5cb8
Source dataset
uspto-grants-2002_11
Patent number
US06479519B1

Reaction notes

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