Water → N,N-Diethyl-4-(2-cyano-4-nitrophenoxy)benzenesulfonamide

HRID 1155740Notes

Reaction equation

HRID 1155740 reaction equation
[CH2:1]([N:3]([CH2:14][CH3:15])[S:4]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:2].[OH-].[Na+].Cl[C:19]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:20]=1[C:21]#[N:22].O>CS(C)=O>[CH2:14]([N:3]([CH2:1][CH3:2])[S:4]([C:7]1[CH:12]=[CH:11][C:10]([O:13][C:19]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:20]=2[C:21]#[N:22])=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 855042-Chloro-5-nitrobenzonitrileHCID 2318424N,N-diethyl-4-hydroxybenzenesulfonamide

Product 1

HCID 12850771N,N-Diethyl-4-(2-cyano-4-nitrophenoxy)benzenesulfonamideYield 88%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6.73 g (0.0294 moles) of N,N-diethyl-4-hydroxybenzenesulfonamide in 150 ml of DMSO was added 1.18 g (0.0294 moles) of NaOH. The mixture was heated to 60° C. and 4.88 g (0.0267 moles) of 2-chloro-5-nitrobenzonitrile was added and the mixture heated at 75° C. for 3 hrs. The reaction mixture was cooled and poured into a solution of 400 ml of 2 N aqueous NaOH and 300 ml of water. The product was collected by filtration, washed well with water and dried to obtain 8.8 g of product (88% yield). Recrystallization from ethanol afforded purified N,N-diethyl-4-(2-cyano-4-nitrophenoxy)benzenesulfonamide, mp 163°-164° C.

Workup

  1. temperaturethe mixture heated at 75° C. for 3 hrs
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe product was collected by filtration
  4. washwashed well with water
  5. customdried

Sources & evidence

ORD record
ord-6a69bb32991f40489e46d5882d87c206
Source dataset
uspto-grants-1982_06
Patent number
US04332820

Reaction notes

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