Sodium Hydroxide → N-(4-nitrobenzyl)methanesulfonamide

HRID 980303Notes

Reaction equation

HRID 980303 reaction equation
[K].[CH3:2][S:3]([NH:6][C:7](=O)[CH3:8])(=[O:5])=[O:4].[N+:10]([C:13]1[CH:20]=[CH:19]C(CBr)=[CH:15][CH:14]=1)([O-:12])=[O:11].[OH-].[Na+]>CN(C=O)C.O>[N+:10]([C:13]1[CH:20]=[CH:19][C:8]([CH2:7][NH:6][S:3]([CH3:2])(=[O:5])=[O:4])=[CH:15][CH:14]=1)([O-:12])=[O:11]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 660114-Nitrobenzyl bromideHCID 88662313N-(methylsulphonyl)acetamide potassium salt

Product 1

HCID 12822520N-(4-nitrobenzyl)methanesulfonamideYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(methylsulphonyl)acetamide potassium salt (23 g) and 4-nitrobenzyl bromide (24 g) in dry DMF (160 ml) was stirred in an oil bath at 130° for 2 h. After standing overnight at room temperature, a solution of sodium hydroxide (8 g) in water (50 ml) was added and the mixture stirred under nitrogen for 0.75 h. The mixture was diluted with water (900 ml) and the product extracted into ethyl acetate (2×400 ml). The combined extract was washed with brine (3×200 ml), dried (Na2SO4) and evaporated in vacuo to leave an orange solid (22 g).

Workup

  1. waitAfter standing overnight at room temperature
  2. stirringthe mixture stirred under nitrogen for 0.75 h
  3. extractionthe product extracted into ethyl acetate (2×400 ml)
  4. extractionThe combined extract
  5. washwas washed with brine (3×200 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-76ae92e70f9b4eeb97ec5098a5379b74
Source dataset
uspto-grants-1987_01
Patent number
US04636521

Reaction notes

Loading…