Diethylamine → N,N-Diethyl-3-nitrobenzenesulfonamide

HRID 1110672Notes

Reaction equation

HRID 1110672 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, 1N 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, 1N 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-aa3aa13b3bb74602b666f316a8a8d088
Source dataset
uspto-grants-1990_12
Patent number
US04976773

Reaction notes

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