Phosphorus sulfide (P2S5) → 6,7-Dimethoxyquinoline-4(1H)-thione

HRID 1433493Notes

Reaction equation

HRID 1433493 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][CH:8]=[CH:7][C:6]2=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:17].C(=O)(O)[O-].[Na+]>COCCOCCOC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][CH:8]=[CH:7][C:6]2=[S:17]

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 4596116,7-Dimethoxy-4-hydroxyquinolineHCID 516892Sodium Bicarbonate

Product 1

HCID 229368096,7-Dimethoxyquinoline-4(1H)-thioneYield 74%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
80 °C

Procedure

After suspending the 6,7-dimethoxy-1H-quinolin-4-one (10.3 g, 50.0 mmol) described in WO9717329, phosphorus pentasulfide (26.7 g, 60.0 mmol) and sodium bicarbonate (26.7 g, 318 mmol) in diglyme (diethyleneglycol dimethyl ether) (100 ml), the suspension was heated and stirred at 80° C. for 2 hours. The reaction solution was returned to room temperature and poured into ice water (1000 ml), and the precipitated crystals were filtered out, washed with water and blow-dried to obtain the title compound (8.19 g, 37.0 mmol, 74%) as yellow crystals.

Workup

  1. temperaturethe suspension was heated
  2. customwas returned to room temperature
  3. filtrationthe precipitated crystals were filtered out
  4. washwashed with water
  5. customblow-dried

Sources & evidence

ORD record
ord-1a33aac849b846f29ac300056fe4b905
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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