Water → HCID 21288004, compound

HRID 868349Notes

Reaction equation

HRID 868349 reaction equation
[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][N:5]=1)[CH3:2].[Cl-].[NH4+].O>C(O)C>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([S:3][CH2:1][CH3:2])=[N:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 107975712-(Ethylthio)-5-nitropyridine

Product 1

HCID 21288004HCID 21288004, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.0 g of 2-ethylthio-5-nitropyridine, 27 g of ammonium chloride, 54 ml of water, and 108 ml of ethanol is heated to 70°-80° C., and 16.2 g of reduced iron is added slowly with stirring. The mixture is stirred at the same temperature for 45 minutes. The hot reaction mixture is filtered, and the filtrate is concentrated. To the residue is added 50 ml of water, and the mixture is extracted with three 50-ml portions of chloroform. The combined extracts are washed with water, dried over magnesium sulfate and concentrated to give 3.7 g of crude 5-amino-2-ethylthiopyridine.

Workup

  1. temperatureis heated to 70°-80° C.
  2. stirringThe mixture is stirred at the same temperature for 45 minutes
  3. filtrationThe hot reaction mixture is filtered
  4. concentrationthe filtrate is concentrated
  5. additionTo the residue is added 50 ml of water
  6. extractionthe mixture is extracted with three 50-ml portions of chloroform
  7. washThe combined extracts are washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d7d91356f9ed48b4b134f007fa5fc333
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

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