Ethyl Acetate → 2-Cyclohexylthio-5-Aminopyridine

HRID 46468Notes

Reaction equation

HRID 46468 reaction equation
[CH:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl-].[NH4+].C(OCC)(=O)C>[Fe].O>[CH:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][N:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 203873472-Cyclohexylthio-5-nitropyridine

Product 1

HCID 203873532-Cyclohexylthio-5-Aminopyridine

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 962WaterSolvent

Procedure

2-Cyclohexylthio-5-nitropyridine (13.4 grams) was added to a suspension of 50 grams of ammonium chloride and 20 grams of powdered iron in a mixture of 220 ml. of ethyl acetate and 30 ml. of water. The reaction mixture was refluxed for 6 hours. TLC indicated some starting material remained. Additional powdered iron (10 grams) was added and the reaction mixture refluxed for another 2 hours. TLC indicated no starting material remaining. The reaction mixture was filtered, taken up in chloroform, washed with water, dried, and evaporated. The main product residue was crystallized from ethyl acetate-hexanes, 8.4 grams of tan crystals; a second crop was crystalled from chloroform-hexanes with charcoal, 0.8 gram. The second crop was analyzed as follows:

Workup

  1. temperatureThe reaction mixture was refluxed for 6 hours
  2. temperaturethe reaction mixture refluxed for another 2 hours
  3. filtrationThe reaction mixture was filtered
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customThe main product residue was crystallized from ethyl acetate-hexanes, 8.4 grams of tan crystals

Sources & evidence

ORD record
ord-f0265b4931ed447fbfc1d0680ebb450b
Source dataset
uspto-grants-1979_11
Patent number
US04173639

Reaction notes

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