Methanesulfonyl chloride → N-(2-methyl-4-nitrobenzyl)methanesulfonamide

HRID 1428760Notes

Reaction equation

HRID 1428760 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][NH2:12].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>N1C=CC=CC=1.ClCCl>[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][NH:12][S:14]([CH3:13])(=[O:16])=[O:15]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 20285976(2-Methyl-4-nitrophenyl)methanamine

Product 1

HCID 86679389N-(2-methyl-4-nitrobenzyl)methanesulfonamideYield 38.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2-methyl-4-nitrophenyl)methanamine (178 mg, 1.071 mmol) in pyridine, cooled to 0° C., were added methane sulfonylchloride (0.16 mL, 2.0349 mmol). The resulting reaction mixture was stirred for 2 h. The mixture dissolved in dichloromethane and washed with 1N HCl. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography to obtain N-(2-methyl-4-nitrobenzyl)methanesulfonamide (100 mg, 38%).

Workup

  1. customThe resulting reaction mixture
  2. washwashed with 1N HCl
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate removed in vacuo
  6. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-2fd1527606ba4919bd226d8bc228d054
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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