Sodium hydride → N-methyl-N-(4-methoxybenzyl)-4-bromophenylsulfonamide

HRID 54984

Reaction equation

HRID 54984 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4].[H-].[Na+].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1>CN(C=O)C>[CH3:1][N:2]([CH2:21][C:20]1[CH:23]=[CH:24][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1)[S:3]([C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 1012154-bromo-N-methylbenzene-1-sulfonamide

Product 1

HCID 8319395N-methyl-N-(4-methoxybenzyl)-4-bromophenylsulfonamideYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-methyl-4-bromophenylsulfonamide (2.5 g, 10 mmol) in DMF (20 mL) at room temperature was added in portions NaH (264 mg, 11 mmol). The mixture was stirred for 45 minutes and then p-methoxybenzylchloride (1.49 mL, 11 mmol) was added dropwise. The mixture was stirred for 1 hour, quenched with water and the precipitate which formed was collected by filtration and dried in vacuo at 60° C. to afford 3.6 g (97%) of N-methyl-N-(4-methoxybenzyl)-4-bromophenylsulfonamide.

Workup

  1. stirringThe mixture was stirred for 1 hour
  2. customquenched with water
  3. customthe precipitate which formed
  4. filtrationwas collected by filtration
  5. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-3068433e0adc427c806d76567bf5cb33
Source dataset
uspto-grants-1997_04
Patent number
US05624922

Linked notes

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