Potassium Hydroxide → HCID 178526679, compound

HRID 601128

Reaction equation

HRID 601128 reaction equation
[N+:1]([C:4]1[C:5](Cl)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].NC(N)=[S:13].[OH-].[K+]>C(O)C>[SH:13][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 796132-Chloro-3-nitropyridineHCID 2723790Thiourea

Product 1

HCID 178526679HCID 178526679, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-mercapto-3-nitropyridine was prepared by treating 3-nitro-2-chloro-pyridine (50 g, 0.0317 mol) with thiourea (24 g, 0.0317 mol) in 200 mL of ethanol at reflux for several hours. After the reaction mixture was allowed to cool, 7.19 mL solution of KOH (42.8 g in 115 mL of water) was added and the resulting mixture was heated at reflux for 3 hours. The crude reaction mixture was cooled to room temperature and then concentrated to 50% of its volume in vacuo. After diluting with 300 mL of water, the product was isolated by vacuum filtration as an orange solid that was used without further purification. MS (DCI/NH3) m/z 157 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ 5.76 (m, 1H), 7.67 (dd, J=8.46, 4.78 Hz, 1H), 8.63 (dd, J=8.46, 1.47 Hz, 1H), 8.73 (dd, J=4.60, 1.65 Hz, 1H).

Workup

  1. temperatureat reflux for several hours
  2. temperatureto cool
  3. temperaturethe resulting mixture was heated
  4. temperatureat reflux for 3 hours
  5. customThe crude reaction mixture
  6. concentrationconcentrated to 50% of its volume in vacuo
  7. additionAfter diluting with 300 mL of water
  8. customthe product was isolated by vacuum filtration as an orange solid that
  9. customwas used without further purification

Sources & evidence

ORD record
ord-75cc0655452c4bdea50cfd6e5a58c3ef
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Linked notes

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