Potassium Carbonate → 2-[1-Methoxy-1-[3-(1,2-dihydro-1-methyl-2-oxoquinolin-3-ylmethoxy)phenyl]propyl]thiazole

HRID 1974499Notes

Reaction equation

HRID 1974499 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)([O:11][CH3:12])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.Br[CH2:19][C:20]1[C:21](=[O:31])[N:22]([CH3:30])[C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:12][O:11][C:8]([C:13]1[S:14][CH:15]=[CH:16][N:17]=1)([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:1][CH2:19][C:20]2[C:21](=[O:31])[N:22]([CH3:30])[C:23]3[C:28]([CH:29]=2)=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:3]=1)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 156373793-[1-Methoxy-1-(1,3-thiazol-2-yl)propyl]phenolHCID 200819733-(Bromomethyl)-1-methyl-2(1H)-quinolinone

Product 1

HCID 191016402-[1-Methoxy-1-[3-(1,2-dihydro-1-methyl-2-oxoquinolin-3-ylmethoxy)phenyl]propyl]thiazoleYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[1-(3-hydroxyphenyl)-1-methoxypropyl]thiazole (0.5 g, 2 mmol), 3-bromomethyl-1,2-dihydro-1-methylquinolin-2-one (0.5 g, 2 mmol), potassium carbonate (0.35 g, 2.5 mmol) and dimethylformamide (3 ml) was stirred at ambient temperature for 48 hours. The mixture was filtered, the filtrate was added to water (30 ml) and the mixture was extracted with ethyl acetate (3×15 ml). The organic extracts were combined, washed with a dilute aqueous sodium hydroxide solution and with a saturated sodium chloride solution, dried (Na2SO4) and evaporated. The residue was purified by column chromatography eluting with toluene/ethyl acetate (7/3 v/v) to give 2-[1-methoxy-1-[3-(1,2-dihydro-1-methyl-2-oxoquinolin-3-ylmethoxy)-phenyl]propyl]thiazole (0.84 g, 100%), m.p. 123°-125° C.

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was added to water (30 ml)
  3. extractionthe mixture was extracted with ethyl acetate (3×15 ml)
  4. washwashed with a dilute aqueous sodium hydroxide solution and with a saturated sodium chloride solution
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography
  8. washeluting with toluene/ethyl acetate (7/3 v/v)

Sources & evidence

ORD record
ord-c7dda33bfee5481a9251ceb52bc567df
Source dataset
uspto-grants-1994_02
Patent number
US05283245

Reaction notes

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