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

HRID 1417859Notes

Reaction equation

HRID 1417859 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4].CNS(C1C=CC(N2CCN(CC[C@H]3C4C(=CC=CC=4)CCO3)CC2)=CC=1)(=O)=O.Cl.CN.C(N(CC)CC)C>C1COCC1>[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 86753846N-Methyl-(S)-(-)-4-[4-[2-(isochroman-1-yl)ethyl]piperazin-1-yl]benzenesulfonamide N-Methyl-4-fluorobenzenesulfonamide

Product 1

HCID 24400544-fluoro-N-methylbenzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-fluorobenzenesulfonyl chloride (III, Aldrich, 3.12 g), methylamine hydrochloride (1.17 g), triethylamine (4.8 ml) and THF (25 ml) are stirred at 20°-25° for five days. The mixture is then partitioned between dichloromethane, aqueous sodium bicarbonate, and saline. The organic phases are dried over magnesium sulfate and concentrated. The resulting solid is crystallized from dichloromethane/hexane and then recrystallized from methanol/dichloromethane to give N-methyl-4-fluorobenzenesulfonamide, NMR 2.67, 4.55, 7.21, 7.89 δ.

Workup

  1. customThe mixture is then partitioned between dichloromethane, aqueous sodium bicarbonate, and saline
  2. dry with materialThe organic phases are dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe resulting solid is crystallized from dichloromethane/hexane
  5. customrecrystallized from methanol/dichloromethane

Sources & evidence

ORD record
ord-7caed63a216645d6bbb3a4f7db62c4de
Source dataset
uspto-grants-1999_03
Patent number
US05877317

Reaction notes

Loading…