4-Nitrobenzenesulfonyl chloride → N,N-Diethyl-4-nitrobenzenesulfonamide

HRID 2186771Notes

Reaction equation

HRID 2186771 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1)([O-:8])=[O:7]>ClCCl>[CH2:1]([N:3]([CH2:4][CH3:5])[S:15]([C:12]1[CH:11]=[CH:10][C:9]([N+:6]([O-:8])=[O:7])=[CH:14][CH:13]=1)(=[O:16])=[O:17])[CH3:2]

Participants

4

Reactant 2

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8021Diethylamine

Product 1

HCID 745341N,N-Diethyl-4-nitrobenzenesulfonamideYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethylamine (0.815 mL, 576 mg, 7.86 mmol) was added in one portion to a solution of 4-nitrobenzenesulfonyl chloride (582 mg, 2.62 mmol) in dichloromethane (10 mL). The resultant solution was stirred at 23° C. for 14 hours and then washed twice with 1N HCl (15 mL). The organics were dried over magnesium sulfate and concentrated to provide N,N-Diethyl-4-nitro-benzenesulfonamide as an off-white solid (617 mg).

Workup

  1. washwashed twice with 1N HCl (15 mL)
  2. dry with materialThe organics were dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-197e5162495f47da885310cfe52b2c72
Source dataset
uspto-grants-2002_06
Patent number
US06407120B1

Reaction notes

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