Methanesulfonyl chloride → N-(2-Fluoro-4-iodophenyl)methanesulfonamide

HRID 2402312

Reaction equation

HRID 2402312 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:10][S:11](Cl)(=[O:13])=[O:12]>N1C=CC=CC=1.O>[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH:4][S:11]([CH3:10])(=[O:13])=[O:12]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 1856942-Fluoro-4-iodoaniline

Product 1

HCID 19785608N-(2-Fluoro-4-iodophenyl)methanesulfonamideYield 75.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of 2-fluoro-4-iodoaniline (5.0 g, 21 mmol) in pyridine (30 mL) at 0° C. was added methanesulfonyl chloride (2.5 mL, 32 mmol) dropwise. The mixture was allowed to warm to ambient temperature and stirred for 3 hours. The mixture was diluted with water and extracted three times with EtOAc. The combined organic extracts were washed with water and brine, dried over Na2SO4, and concentrated. Purification by chromatography (SiO2, 33% EtOAc/Hexanes) afforded the title compound (5.0 g, 75% yield). 1H NMR (300 MHz, DMSO-d6) δ 9.70 (s, 1H), 7.71 (dd, J=9.9, 1.9 Hz, 1H), 7.56 (ddd, J=8.4, 1.9, 1.0 Hz, 1H), 7.19 (t, J=8.4 Hz, 1H), 3.03 (s, 3H); MS (ESI; M−H) m/z 314.

Workup

  1. extractionextracted three times with EtOAc
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by chromatography (SiO2, 33% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-f490f36745af4f2a9b39ccdfae92449f
Source dataset
uspto-grants-2014_08
Patent number
US08796328B2

Linked notes

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