Water → 3-[4-(3,5-Dichloro-2-hydroxy benzenesulfonamido)-benzenesulfonyl]acrylonitrile

HRID 267586Notes

Reaction equation

HRID 267586 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]=[CH:12][C:13]#[N:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH:15][C:16]1[C:21]([Cl:22])=[CH:20][C:19]([Cl:23])=[CH:18][C:17]=1[S:24](Cl)(=[O:26])=[O:25].O>O1CCOCC1>[Cl:22][C:21]1[C:16]([OH:15])=[C:17]([S:24]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([S:8]([CH:11]=[CH:12][C:13]#[N:14])(=[O:10])=[O:9])=[CH:6][CH:7]=2)(=[O:26])=[O:25])[CH:18]=[C:19]([Cl:23])[CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideHCID 545613262-Cyanovinyl 4-aminophenyl sulfone

Product 1

HCID 537403313-[4-(3,5-Dichloro-2-hydroxy benzenesulfonamido)-benzenesulfonyl]acrylonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 4.2 g (0.02 mol) of 3-(4-aminobenzenesulfonyl)acrylonitrile in 40 ml of dioxane (containing 1.6 ml pyridine) is added a solution of 5.3 g (0.02 mol) of 2-hydroxy-3,5-dichlorobenzenesulfonyl chloride in 15 ml dioxane. The second solution is slowly added to the first over a 10-minute period. The reaction mixture (which takes on an orange color) is stirred for 2 hours at room temperature and then left for 16 hours. Water is added and the precipitate is filtered off and dried, giving the pink, fluffy 3-[4-(3,5-dichloro-2-hydroxy benzenesulfonamido)-benzenesulfonyl]acrylonitrile: ##SPC28##

Workup

  1. additionThe second solution is slowly added to the first over a 10-minute period
  2. waitleft for 16 hours
  3. filtrationthe precipitate is filtered off
  4. customdried

Sources & evidence

ORD record
ord-451461c0ac414c9dbfc0d1da33abb148
Source dataset
uspto-grants-1976_03
Patent number
US03943154

Reaction notes

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