Thiourea → 7-Nitroquinoline-4(1H)-thione

HRID 965004Notes

Reaction equation

HRID 965004 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.NC(N)=[S:17]>C(O)C>[N+:12]([C:8]1[CH:7]=[C:6]2[C:11]([C:2](=[S:17])[CH:3]=[CH:4][NH:5]2)=[CH:10][CH:9]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 123225804-Chloro-7-nitroquinoline

Product 1

HCID 190750667-Nitroquinoline-4(1H)-thione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

4-Chloro-7-nitroquinoline (100 mg, 0.48 mmol) and thiourea (100 mg, 1.3 mmol) were added to ethanol (50 ml) and stirred at 80° C. for 30 minutes. After allowing to cool to room temperature, ethanol was removed under reduced pressure. The residue was chromatographed by silica gel column chromatography and eluted with mixed solution of methylene chloride with methanol (19 : 1) for collection of yellow bands. The solvent was removed to obtain 7 mg (7%) of the titled yellow compound.

Workup

  1. temperatureto cool to room temperature
  2. customethanol was removed under reduced pressure
  3. customThe residue was chromatographed by silica gel column chromatography
  4. washeluted with mixed solution of methylene chloride with methanol (19 : 1) for collection of yellow bands
  5. customThe solvent was removed
  6. customto obtain 7 mg (7%) of the titled yellow compound

Sources & evidence

ORD record
ord-a6262e162148456bb565a1479526dd3f
Source dataset
uspto-grants-1998_06
Patent number
US05773449

Reaction notes

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