Diethylamine → N,N-Diethyl-3-nitrobenzenesulfonamide

HRID 1591014Notes

Reaction equation

HRID 1591014 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[N+:6]([C:9]1[CH:10]=[C:11]([S:15](Cl)(=[O:17])=[O:16])[CH:12]=[CH:13][CH:14]=1)([O-:8])=[O:7]>N1C=CC=CC=1.C(Cl)Cl>[CH2:1]([N:3]([CH2:4][CH3:5])[S:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([N+:6]([O-:8])=[O:7])[CH:10]=1)(=[O:16])=[O:17])[CH3:2]

Participants

5

Reactant 2

HCID 8021DiethylamineHCID 84763-Nitrobenzenesulfonyl chloride

Product 1

HCID 232031N,N-Diethyl-3-nitrobenzenesulfonamideYield 51.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Diethylamine (2.4 g) was dissolved in pyridine (15 ml) and 3-nitrobenzenesulfonyl chloride (6.7 g) was added, followed by stirring at 50° C for 2 hours. The residue obtained by an evaporation of pyridine under a reduced pressure was dissolved in methylene chloride (150 ml), washed with water, 1 N hydrochloric acid, water, and saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. Evaporation of the solvent under a reduced pressure gave N,N-diethyl-3-(nitro)benzenesulfonamide (4.0 g).

Workup

  1. washwashed with water, 1 N hydrochloric acid, water, and saturated aqueous sodium chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. customEvaporation of the solvent under a reduced pressure

Sources & evidence

ORD record
ord-01ddd29617784e7e8064d8c0444b337e
Source dataset
uspto-grants-1993_04
Patent number
US05205855

Reaction notes

Loading…