Methylamine → 4-fluoro-N-methylbenzene-1-sulfonamide

HRID 496595

Reaction equation

HRID 496595 reaction equation
CN.[CH2:3]([N:5](CC)CC)C.[F:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>O1CCCC1.C(Cl)Cl>[CH3:3][NH:5][S:17]([C:14]1[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chloride

Product 1

HCID 24400544-fluoro-N-methylbenzene-1-sulfonamideYield 95.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 125 ml of methylamine (0.25 molar) in tetrahydrofuran and 13.9 ml (0.10 mol) of triethylamine was chilled in an ice bath. To this chilled solution was added dropwise 19.4 g (0.10 mol) of 4-fluorobenzenesulfonyl chloride in 150 ml of CH2Cl2 was added and the mixture refluxed for 2 hours and then stirred overnight at room temperature. The mixture was with CH2Cl2, washed with H2O, 2N citric acid, brine and dried (Na2SO4). The solution was filtered through a pad of hydrous magnesium silicate and the filtrate concentrated to dryness under vacuum to give 18.0 g of white solid, mp 67-70° C.

Workup

  1. temperaturewas chilled in an ice bath
  2. additionwas added
  3. temperaturethe mixture refluxed for 2 hours
  4. washwashed with H2O, 2N citric acid, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationThe solution was filtered through a pad of hydrous magnesium silicate
  7. concentrationthe filtrate concentrated to dryness under vacuum

Sources & evidence

ORD record
ord-76b8047aab694b01b80a5d6ed2ffd4d9
Source dataset
uspto-grants-2005_09
Patent number
US06946473B2

Linked notes

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