Ammonium Hydroxide → 2-Chloro-4-(2-methyl-3-oxobutan-2-yl)benzenesulfonamide

HRID 83870Notes

Reaction equation

HRID 83870 reaction equation
[NH4+:1].[OH-].[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([CH3:15])([C:12](=[O:14])[CH3:13])[CH3:11])[CH:7]=[CH:6][C:5]=1[S:16](Cl)(=[O:18])=[O:17]>C1COCC1>[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([CH3:15])([C:12](=[O:14])[CH3:13])[CH3:11])[CH:7]=[CH:6][C:5]=1[S:16]([NH2:1])(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 866622492-Chloro-4-(2-methyl-3-oxobutan-2-yl)benzene-1-sulfonyl chloride

Product 1

HCID 667399922-Chloro-4-(2-methyl-3-oxobutan-2-yl)benzenesulfonamideYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of NH4OH (30 mL) was added a solution of 2-chloro-4-(2-methyl-3-oxobutan-2-yl)benzene-1-sulfonyl chloride (9.8 g, 33.2 mmol) in THF (150 mL) at 0° C. After stirring 2 h, volatiles were removed under reduced pressure. The residue was diluted with water and extracted with EtOAc (100 mL×2). The combined extracts were dried over MgSO4, concentrated and purified by column chromatography (Hex/EtOAc=4:1 to 2:1) to give 2-chloro-4-(2-methyl-3-oxobutan-2-yl)benzenesulfonamide (8.9 g, 96% yield) as yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.09 (d, J=8.4 Hz, 1H), 7.43 (s, 1H), 7.27 (d, J=2.2 Hz, 1H), 5.09 (s, 2H), 2.04 (s, 3H), 1.52 (s, 6H).

Workup

  1. customvolatiles were removed under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted with EtOAc (100 mL×2)
  4. dry with materialThe combined extracts were dried over MgSO4
  5. concentrationconcentrated
  6. custompurified by column chromatography (Hex/EtOAc=4:1 to 2:1)

Sources & evidence

ORD record
ord-7c771fab76c743ceb1ee74ac1d5e0e90
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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