Sodium hydride → 4-tert-butyl-N-(6-chloropyrimidin-4-yl)benzenesulfonamide

HRID 2307

Reaction equation

HRID 2307 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[C:9]([C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10].[H-].[Na+]>CN(C)C=O.Cl.O>[C:9]([C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:22][C:6]2[CH:7]=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=2)(=[O:20])=[O:21])=[CH:15][CH:14]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 709434,6-DichloropyrimidineHCID 2228724-tert-Butylbenzenesulfonamide

Product 1

HCID 108710784-tert-butyl-N-(6-chloropyrimidin-4-yl)benzenesulfonamideYield 69.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4,6-dichloropyrimidine (1.33 g) and 4-tert-butylbenzenesulfonamide (1.96 g) in dimethylformamide (20 ml) is added sodium hydride (60% dispersion-type, 714 mg). The mixture is stirred at room temperature for two hours, and the reaction solution is diluted with 10% hydrochloric acid and water. The mixture is extracted with ethyl acetate, and the ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is recrystallized from ethyl acetate to give 4-tert-butyl-N-(6-chloropyrimidin-4-yl)benzenesulfonamide (2.02 g).

Workup

  1. extractionThe mixture is extracted with ethyl acetate
  2. washthe ethyl acetate layer is washed
  3. customdried
  4. customevaporated
  5. customto remove the solvent
  6. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6c62f99d0fed4032b2e1262e33a10198
Source dataset
uspto-grants-1998_03
Patent number
US05728706

Linked notes

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