Pyridine → HCID 22272548, compound

HRID 346786Notes

Reaction equation

HRID 346786 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15]1(N)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.[N:26]1C=CC=CC=1>C(Cl)Cl>[C:20]1([C:4]2[C:3]([N+:12]([O-:14])=[O:13])=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=2[S:8]([NH2:26])(=[O:10])=[O:9])[C:19]2[C:24](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 86401-Naphthylamine

Product 1

HCID 22272548HCID 22272548, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chloro-3-nitrobenzenesulphonyl chloride (0.992 g, 3.87 mmol) was added to a solution of naphthalen-1-ylamine (0.665 g, 4.64 mmol) and pyridine (3.1 mL, 38.7 mmol) dissolved in DCM (5 mL). The solution was stirred at room temperature for 2 days and the volatiles were evaporated. The crude mixture was dissolved in EtOAc and the organic phase was washed with 1 N HCl, dried with MgSO4, filtered and concentrated to give 1.1 g of naphthalen-1-yl-3-nitro-4-chloro-benzenesulphonamide. Naphthalen-1-yl-3-nitro-4-chloro-benzenesulphonamide was dissolved in CH3CN (10 mL) and piperazine (0.683 g, 7.93 mmol) was added. The mixture was stirred at 65° C. for 16 hours. The mixture was concentrated and the crude product was purified by flash chromatography on silica using DCM→DCM/MeOH (10%)+aqueous NH3 (0.4 as eluent to give 0.531 g of the free base which was converted to its HCl-salt.

Workup

  1. customthe volatiles were evaporated
  2. dissolutionThe crude mixture was dissolved in EtOAc
  3. washthe organic phase was washed with 1 N HCl
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-354f7e2c952f495cab8e48e149ff905c
Source dataset
uspto-grants-2007_02
Patent number
US07173035B2

Reaction notes

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