Methylamine → 3-bromo-N-methyl-5-(trifluoromethyl)benzenesulfonamide

HRID 733188Notes

Reaction equation

HRID 733188 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:12](Cl)(=[O:14])=[O:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH3:16][NH2:17]>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([S:12]([NH:17][CH3:16])(=[O:14])=[O:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 27786103-Bromo-5-(trifluoromethyl)benzenesulfonyl chloride

Product 1

HCID 670589193-bromo-N-methyl-5-(trifluoromethyl)benzenesulfonamideYield 92%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-bromo-5-(trifluoromethyl)-benzene sulphonyl chloride (200 mg) in 1,4-dioxane (1 mL) was added methylamine (40% aqueous solution, 96 mg). The mixture was stirred at room temperature for three hours then diluted with ethyl acetate (20 mL) and washed with HCl (1M, 2×20 mL). Organics were separated, dried over sodium sulphate, filtered, and solvent was removed under reduced pressure to yield 3-bromo-N-methyl-5-trifluoromethyl-benzenesulphonamide (181 mg) as a yellow solid. 1H NMR (MeOD): δ 8.19 (s, 1H), 8.05 (s, 1H), 7.98 (s, 1H), 4.58 (m, 1H), 2.74 (d, 3H). MS m/z 319.8 (M+1).

Workup

  1. washwashed with HCl (1M, 2×20 mL)
  2. customOrganics were separated
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customsolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f04f4542283d49d89f76204e01ab3a20
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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