Methanesulfonyl chloride → N-(3-methyl-5-nitro-phenyl)-methylsulfonamide

HRID 1957961Notes

Reaction equation

HRID 1957961 reaction equation
CS([C:5]1[CH:6]=[C:7]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[NH2:8])(=O)=O.[CH3:15][S:16](Cl)(=[O:18])=[O:17].[C:20]([O-])(O)=O.[Na+]>N1C=CC=CC=1>[CH3:20][C:5]1[CH:6]=[C:7]([NH:8][S:16]([CH3:15])(=[O:18])=[O:17])[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 673593153-(Methanesulfonyl)-5-nitroaniline

Product 1

HCID 68423293N-(3-methyl-5-nitro-phenyl)-methylsulfonamideYield 43%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

3-methylsulfonyl-5-nitro-aniline (0.26 g; 1.2 mmol) was dissolved in pyridine (10 ml). A solution of methanesulfonylchloride (0.2 mL; 2.4 mmol) in 2 mL of pyridine was added and the reaction mixture was stirred for 12 hours at ambient temperature. NaHCO3 solution was added and the mixture extracted with dichloromethane. The aqueous phase was acidified and extracted with ethyl acetate. The organic phase was dried and concentrated. 0.12 g (0.5 mmol; 43% yield) of N-(3-methyl-5-nitro-phenyl)-methylsulfonamide were obtained as a yellow solid.

Workup

  1. extractionthe mixture extracted with dichloromethane
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b64b62ebbc50474a8949d1520ca0cbd1
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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