Ethyl Acetate → 6,7-Dimethoxy-4-(5-nitrothiazol-2-ylsulfanyl)quinoline

HRID 1433499Notes

Reaction equation

HRID 1433499 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=[S:15].Br[C:17]1[S:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][N:21]=1.C(OCC)(=O)C.[OH-].[Na+]>CN(C)C=O.CCCCCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[S:15][C:17]1[S:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][N:21]=1

Participants

7

Reactant 4

HCID 8857Ethyl Acetate2×HCID 14798Sodium HydroxideHCID 182112-Bromo-5-nitrothiazoleHCID 229368096,7-Dimethoxyquinoline-4(1H)-thione

Product 1

HCID 229367196,7-Dimethoxy-4-(5-nitrothiazol-2-ylsulfanyl)quinolineYield 49%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

After suspending 6,7-dimethoxy-1H-quinoline-4-thione (2.21 g, 10.0 mmol) in dimethylformamide (30 ml), 2-bromo-5-nitrothiazole (2.30 g, 11.0 mmol) was added at 0° C., and then the mixture was stirred at room temperature for 1 hour. The reaction solution was distributed between ethyl acetate and 1N aqueous sodium hydroxide, the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent—ethyl acetate:hexane=3:1), and the fraction containing the target substance was concentrated, suspended in ethyl acetate and diluted with hexane, after which the crystals were filtered out, washed with hexane and then blow-dried to obtain the title compound (1.70 g, 4.87 mmol, 49%) as light yellow crystals.

Workup

  1. additionwas added at 0° C.
  2. washthe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationthe drying agent was filtered off
  5. distillationthe filtrate was distilled off under reduced pressure
  6. customThe obtained crude product
  7. additionthe fraction containing the target substance
  8. concentrationwas concentrated
  9. additiondiluted with hexane
  10. filtrationafter which the crystals were filtered out
  11. washwashed with hexane
  12. customblow-dried

Sources & evidence

ORD record
ord-3502d2aafc1d4ef88caf57e3ba5fe6d4
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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