Diethylamine → N,N-diethyl-2-nitrobenzenesulfonamide

HRID 847653Notes

Reaction equation

HRID 847653 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[CH2:14]([NH:16][CH2:17][CH3:18])[CH3:15].Cl.C(NCC)C>O1CCCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:16]([CH2:17][CH3:18])[CH2:14][CH3:15])(=[O:12])=[O:11])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 10197650Diethylammonium chloride

Product 1

HCID 4229519N,N-diethyl-2-nitrobenzenesulfonamideYield 79.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 132.6 g of o-nitrobenzenesulfonyl chloride in 700 ml of tetrahydrofuran was added 88.5 g of diethylamine at 5°-15°. The reaction mixture was stirred at room temperature for 1 hour before the precipitated diethylamine hydrochloride was removed by filtration. The filtrate was evaporated to dryness in-vacuo and the residue dissolved in 1-chlorobutane. The 1-chlorobutane solution was washed with water, dried over magnesium sulfate and evaporated in-vacuo to give 122.4 g of o-nitro-N,N-diethylbenzenesulfonamide as a dark oil.

Workup

  1. customwas removed by filtration
  2. customThe filtrate was evaporated to dryness in-vacuo
  3. dissolutionthe residue dissolved in 1-chlorobutane
  4. washThe 1-chlorobutane solution was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in-vacuo

Sources & evidence

ORD record
ord-d58875a01e36460ea4df9c3969887d28
Source dataset
uspto-grants-1981_10
Patent number
US04293330

Reaction notes

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