Pyridine → HCID 67046906, compound

HRID 607522Notes

Reaction equation

HRID 607522 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([I:9])[C:6]([F:10])=[CH:5][C:3]=1[NH2:4].[CH3:11][S:12](Cl)(=[O:14])=[O:13].N1C=CC=CC=1>C(Cl)Cl>[F:1][C:2]1[CH:8]=[C:7]([I:9])[C:6]([F:10])=[CH:5][C:3]=1[NH:4][S:12]([CH3:11])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 18960027HCID 18960027, compound

Product 1

HCID 67046906HCID 67046906, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,5-difluoro-4-iodoaniline (5.3 g, 19.4 mmol, Can. J. Chem., 2000(78), 1081-1088) in DCM (50 ml) was added methanesulfonyl chloride (1.65 ml, 21.3 mmol) and pyridine (4.7 ml, 58.2 mmol) at 0° C. The mixture was stirred for 24 hours at room temperature. The mixture was partitioned between EtOAc and 2 M HCl aqueous solution. The organic layer was separated and washed with 2 M aqueous HCl solution and brine, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by silica gel column chromatography eluting with gradually from hexane/EtOAc (4:1) to hexane/EtOAc (3:1) to give the title compound (5.6 g, 87%) as purple solids.

Workup

  1. customThe mixture was partitioned between EtOAc and 2 M HCl aqueous solution
  2. customThe organic layer was separated
  3. washwashed with 2 M aqueous HCl solution and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel column chromatography
  7. washeluting with gradually from hexane/EtOAc (4:1) to hexane/EtOAc (3:1)

Sources & evidence

ORD record
ord-7d6a0284c3bb4402aae34912958729cb
Source dataset
uspto-grants-2011_03
Patent number
US07915448B2

Reaction notes

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