Benzenamine hydrochloride (1:1) → 2-Chloro-5-(2-oxo-propyl)-N-phenyl-benzenesulfonamide

HRID 2382593Notes

Reaction equation

HRID 2382593 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O-])([O-])=O.[Na+].[Na+].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](=[O:25])[CH3:24])=[CH:18][C:17]=1[S:26](Cl)(=[O:28])=[O:27]>O1CCOCC1.O>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](=[O:25])[CH3:24])=[CH:18][C:17]=1[S:26]([NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)(=[O:27])=[O:28]

Participants

6

Reactant 3

HCID 8870Benzenamine hydrochloride (1:1)HCID 10340Sodium CarbonateHCID 578311052-Chloro-5-(2-oxopropyl)benzene-1-sulfonyl chloride2×

Product 1

HCID 687249242-Chloro-5-(2-oxo-propyl)-N-phenyl-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Aniline hydrochloride (64.8 mg, 0.05 mmol) is dissolved in 1,4-dioxane (1 ml) in a reaction tube and Na2CO3(85 mg) dissolved in water (0.5 ml) is added. To this mixture is added 2-Chloro-5-(2-oxo-propyl)-benzenesulfonyl chloride (115 mg, 0.43 mmol) (Intermediate A, prepared as described in WO03072557, page 77) in 1,4-dioxane (1 ml). The reaction mixture is left at room temperature overnight and monitored by LC-MS. The reaction mixture is shaken overnight with amino polystyrene (300 mg) and macroporous-isocyanate (300 mg), filtered and the resin is washed with MeOH (0.5 ml). The filtrate is concentrated in vacuo to afford the title compound.

Workup

  1. additionis added
  2. filtrationfiltered
  3. washthe resin is washed with MeOH (0.5 ml)
  4. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-ae87fbc945aa4b53b17eb65d9c0788f5
Source dataset
uspto-grants-2012_09
Patent number
US08263585B2

Reaction notes

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