Methylamine → 5-fluoro-N-methyl-2-nitrobenzene-1-sulfonamide

HRID 77382Notes

Reaction equation

HRID 77382 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([S:8](Cl)(=[O:10])=[O:9])[CH:7]=1.[CH3:15][NH2:16].O1CCCC1>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([S:8]([NH:16][CH3:15])(=[O:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 129043685-Fluoro-2-nitrobenzene-1-sulfonyl chloride

Product 1

HCID 671149565-fluoro-N-methyl-2-nitrobenzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-fluoro-2-nitrobenzene-1-sulfonyl chloride (2.0 g, 8.35 mmol) in dichloromethane (50 mL) was cooled using an ice water bath. 2M methylamine in tetrahydrofuran (5.0 mL, 10.0 mmol) was added. The resulting solution was stirred for 2 hours. The reaction mixture was washed with 2N HCl solution (2×100 mL), brine (100 mL) and then dried over magnesium sulphate. The solution was filtered before concentrating under reduced pressure to afford 5-fluoro-N-methyl-2-nitrobenzenesulfonamide (1.79 g, 7.64 mmol).

Workup

  1. washThe reaction mixture was washed with 2N HCl solution (2×100 mL), brine (100 mL)
  2. dry with materialdried over magnesium sulphate
  3. filtrationThe solution was filtered
  4. concentrationbefore concentrating under reduced pressure

Sources & evidence

ORD record
ord-78d01554a28249009d4852ceca6c6663
Source dataset
uspto-grants-2014_09
Patent number
US08841289B2

Reaction notes

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