Water → HCID 67010359, compound

HRID 2194515Notes

Reaction equation

HRID 2194515 reaction equation
Br[CH2:2][N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][N:11]=2)[CH:6]=[C:5]([C:13]([O:15][CH3:16])=[O:14])[C:4]1=[O:17].[CH2:18]([SH:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:18]([S:20][CH2:2][N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][N:11]=2)[CH:6]=[C:5]([C:13]([O:15][CH3:16])=[O:14])[C:4]1=[O:17])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 67009622HCID 67009622, compound

Product 1

HCID 67010359HCID 67010359, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.00 g (10.1 mmol) of methyl 1-(bromomethyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate was dissolved in N,N-dimethylformamide (40 mL), and 0.94 g (15.1 mmol) of ethanethiol and 2.09 g (15.1 mmol) of potassium carbonate were added to the solution. The resulting mixture was stirred overnight at room temperature. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic phase was washed with water, dried, and concentrated. Thus, 2.85 g (yield: quantitative) of the title compound was obtained as pale yellow crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5d01ee96739f476e8538475db0c6f676
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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