Methylamine → 4-Methoxy-N-methylbenzenesulfonamide

HRID 352398Notes

Reaction equation

HRID 352398 reaction equation
[CH2:1]([N:3](CC)CC)C.CN.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>O1CCCC1>[CH3:1][NH:3][S:18]([C:15]1[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 24974294-Methoxy-N-methylbenzenesulfonamideYield 91.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Part A: To a mixture of 50 mL of tetrahydrofuran, 15 mL (108 mmol) of triethylamine and 10 mL (116 mmol) of a 40% aqueous methylamine solution at 0 C, was added 15.0 g (72.6 mmol) of 4-methoxy-benzenesulfonyl chloride over a 15 minutes. After 1 hour, the solvents were removed in vacuo, 5% aqueous KHSO4 and ethyl acetate added, the organic layer separated, washed with saturated aqueous sodium bicarbonate, brine, dried with sodium sulfate, filtered and stripped to afford a white solid. This was recrystallized from hot ethyl acetate/hexane to afford 13.4 g of N-methyl-4-methoxybenzenesulfonamide, m/e=202 (M+H).

Workup

  1. customthe solvents were removed in vacuo, 5% aqueous KHSO4 and ethyl acetate
  2. additionadded
  3. customthe organic layer separated
  4. washwashed with saturated aqueous sodium bicarbonate, brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customto afford a white solid
  8. customThis was recrystallized from hot ethyl acetate/hexane

Sources & evidence

ORD record
ord-92aa8303f6944230bdc0dd1fc11ebed3
Source dataset
uspto-grants-2004_06
Patent number
US06747027B1

Reaction notes

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