Ammonia → 2-Chloro-5-(2-oxo-propyl)-benzenesulfonamide

HRID 908169Notes

Reaction equation

HRID 908169 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][C:3]=1[S:12](Cl)(=[O:14])=[O:13].C(=O)([O-])[O-].[Na+].[Na+].[NH3:22]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][C:3]=1[S:12]([NH2:22])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 10340Sodium CarbonateHCID 578311052-Chloro-5-(2-oxopropyl)benzene-1-sulfonyl chloride

Product 1

HCID 673923132-Chloro-5-(2-oxo-propyl)-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

2-Chloro-5-(2-oxopropyl)-benzenesulphonyl chloride (32a) (2.0 g, 7.5 mmol) is dissolved in dioxan (50 ml) with stirring. Sodium carbonate (7.5 ml, 2M solution, 2 eq.) is added followed by a solution of ammonia in dioxan (37.5 ml, 0.5 M). After 30 min the reaction mixture is poured onto water (250 ml) and extracted with ethyl acetate (3×100 ml). The combined organic extracts are washed with water (2×100 ml) followed by brine (100 ml) and dried (MgSO4). After filtration the solvent is removed and the product is purified by chromatography on silica, eluting with ethyl acetate/hexane (1:2) to afford the titled compound.

Workup

  1. additionAfter 30 min the reaction mixture is poured onto water (250 ml)
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. washThe combined organic extracts are washed with water (2×100 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationAfter filtration the solvent
  6. customis removed
  7. customthe product is purified by chromatography on silica
  8. washeluting with ethyl acetate/hexane (1:2)

Sources & evidence

ORD record
ord-53f1827dc92440a48ac6749622b429ee
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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