Water → HCID 71252464, compound

HRID 2411358Notes

Reaction equation

HRID 2411358 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N:3]=1.[S:12]1(=[O:18])(=[O:17])[CH2:16][CH2:15][CH2:14][NH:13]1.[H-].[Na+].O>CN(C)C=O>[O:17]=[S:12]1(=[O:18])[CH2:16][CH2:15][CH2:14][N:13]1[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 6421571,3-PropanesultamHCID 12627752Methyl 2-chloropyrimidine-5-carboxylate

Product 1

HCID 71252464HCID 71252464, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 2-chloropyrimidine-5-carboxylate (173 mg) and isothiazolidine 1,1-dioxide (145 mg) were dissolved in N,N-dimethylformamide (1 mL), and sodium hydride (48 mg, 60% in oil) was added under ice-cooling. After stirring at room temperature for 6 hr, water was added, and the mixture was extracted with ethyl acetate. The solvent was evaporated, diisopropyl ether and ethyl acetate were added, and the precipitated solid was collected by filtration to give the title compound (185 mg).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe solvent was evaporated
  4. additiondiisopropyl ether and ethyl acetate were added
  5. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-a52f2fdd8af94311ab3c8a20e6f1fcbd
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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