Dimethylamine → 2-nitrobenzyl-N,N-dimethylsulfonamide

HRID 23394

Reaction equation

HRID 23394 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][S:11](Cl)(=[O:13])=[O:12])([O-:3])=[O:2].[CH3:15][NH:16][CH3:17]>O1CCOCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][S:11]([N:16]([CH3:17])[CH3:15])(=[O:13])=[O:12])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 4305447(2-nitrophenyl)methanesulfonyl Chloride

Product 1

HCID 131787262-nitrobenzyl-N,N-dimethylsulfonamideYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Nitro-α-toluenesulfonyl chloride (0.943 g, 4.0 mmole) was dissolved in dry dioxane (7 ml) and treated with a solution of dimethylamine (4 ml 2M solution in THF, 8.0 mmole), and stirred at room temperature for a total of 6 h. The reaction mixture was transferred to a separatory funnel and partitioned between ethyl acetate and water. The organic solution was washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness to afford the pure 2-nitrobenzyl-N,N-dimethylsulfonamide, 0.829 g (85% yield).

Workup

  1. customThe reaction mixture was transferred to a separatory funnel
  2. custompartitioned between ethyl acetate and water
  3. washThe organic solution was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-72587823e0244b7bbf8e4b0bdd642b13
Source dataset
uspto-grants-2005_02
Patent number
US06852726B2

Linked notes

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