Water → HCID 12850770, compound

HRID 1155739Notes

Reaction equation

HRID 1155739 reaction equation
[CH3:1][N:2]([CH3:13])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4].[OH-].[Na+].Cl[C:17]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:18]=1[C:19]#[N:20].O>CS(C)=O>[CH3:1][N:2]([CH3:13])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][C:17]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:18]=2[C:19]#[N:20])=[CH:8][CH:7]=1)(=[O:4])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 84760Benzenesulfonamide, 4-hydroxy-N,N-dimethyl-HCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 12850770HCID 12850770, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6.37 g (0.0317 moles) of N,N-dimethyl-4-hydroxybenzenesulfonamide in 150 ml of DMSO was added 1.27 g (0.0317 moles) of NaOH. The mixture was heated to 60° C. and 5.26 g (0.288 moles) of 2-chloro-5-nitrobenzonitrile added and the mixture heated at 75° C. for 21/2 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 a mixture of ethanol and dimethylformamide afforded purified N,N-dimethyl-4-(2-cyano-4-nitrophenoxy)benzenesulfonamide, mp 221.5°-223° C.

Workup

  1. temperaturethe mixture heated at 75° C. for 21/2 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-3122a2461cee44ba8a42835f61bd4ef9
Source dataset
uspto-grants-1982_06
Patent number
US04332820

Reaction notes

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