Pyridine → 2-Chloro-N-(3-cyano-phenyl)-5-(2-oxo-propyl)-benzenesulfonamide

HRID 2382594Notes

Reaction equation

HRID 2382594 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].N1C=CC=CC=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24](=[O:26])[CH3:25])=[CH:19][C:18]=1[S:27](Cl)(=[O:29])=[O:28]>O1CCOCC1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24](=[O:26])[CH3:25])=[CH:19][C:18]=1[S:27]([NH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[CH:3]=1)(=[O:28])=[O:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 167023-AminobenzonitrileHCID 578311052-Chloro-5-(2-oxopropyl)benzene-1-sulfonyl chloride2×

Product 1

HCID 687243222-Chloro-N-(3-cyano-phenyl)-5-(2-oxo-propyl)-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Aminobenzonitrile (442 mg, 3.7 mmol, 1 eq) is dissolved in dry pyridine (606 ul, 7.5 mmol, 2 eq), under an inert atmosphere of argon. 2-Chloro-5-(2-oxo-propyl)-benzenesulfonyl chloride (Intermediate A)(1.0 g, 3.7 mmol) in 1,4-dioxane (2 ml) is added and the reaction mixture is stirred at room temperature overnight. The solvents are removed in vacuo and the residue is dissolved in DCM and 0.5M HCl. The phases are separated and the organic portion is washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound.

Workup

  1. customThe solvents are removed in vacuo
  2. dissolutionthe residue is dissolved in DCM
  3. customThe phases are separated
  4. washthe organic portion is washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-31e099c231854d93a82795a16f863e3c
Source dataset
uspto-grants-2012_09
Patent number
US08263585B2

Reaction notes

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