Methanesulfonyl chloride → Methanesulfonamide, N-[2-iodo-4-(trifluoromethyl)phenyl]-

HRID 1171463Notes

Reaction equation

HRID 1171463 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH2:12].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[I:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][S:14]([CH3:13])(=[O:16])=[O:15]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 27833222-Iodo-4-(trifluoromethyl)aniline

Product 1

HCID 21075164Methanesulfonamide, N-[2-iodo-4-(trifluoromethyl)phenyl]-Yield 32.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 2-iodo-4-(trifluoromethyl)benzenamine (11.0 g, 0.0382 mol), pyridine (40 ml), methanesulfonylchloride (5.3 g, 0.046 mol) and DMAP (0.46 g, 0.0038 mol) in a 100 ml RB flask was heated slowly to 105° C. and maintained the same temperature for over night. The reaction mixture was concentrated to remove the pyridine. The crude product obtained was purified by column chromatography using 10% ethyl acetate in pet ether as eluent to get N-(2-iodo-4-(trifluoromethyl)phenyl)methanesulfonamide (4.5 g, 32%) as white solid. 1H NMR (400 MHz, CDCl3) δ 3.08 (s, 3H), 6.88 (bs, 1H), 7.65 (d, 1H), 7.75 (d, 1H), 8.07 (s, 1H).

Workup

  1. temperaturemaintained the same temperature for over night
  2. concentrationThe reaction mixture was concentrated
  3. customto remove the pyridine
  4. customThe crude product obtained
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-c136f2dc6bfb4c35bc68c185cd013f30
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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