Water → 3-[4-(4-Carbethoxybenzenesulfonamido)benzenesulfonyl]acrylonitrile

HRID 267589Notes

Reaction equation

HRID 267589 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.O.C(=O)(O)[O-].[Na+].[C:21]([C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1)([O:23][CH2:24][CH3:25])=[O:22]>CC(C)=O>[C:21]([C:26]1[CH:31]=[CH:30][C:29]([S:32]([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:33])=[O:34])=[CH:28][CH:27]=1)([O:23][CH2:24][CH3:25])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 3667622Ethyl 4-(chlorosulfonyl)benzoateHCID 545613262-Cyanovinyl 4-aminophenyl sulfone

Product 1

HCID 544544983-[4-(4-Carbethoxybenzenesulfonamido)benzenesulfonyl]acrylonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

6.3 grams (0.03 mol) of 3-(4-aminobenzenesulfonyl)acrylonitrile are dissolved in 70 ml of acetone, and 30 ml water are added thereto. Sodium bicarbonate (2.6 g, 0.03 mol) is added with stirring, followed by a solution of 7 g (0.03 mol) of 4-carbethoxybenzenesulfonyl chloride in 30 ml acetone. The reaction mixture is stirred overnight, filtered and the filtrate diluted with 750 ml water. The dark, cream-colored solid which separates and which is recovered by filtration and drying constitutes 3-[4-(4-carbethoxyxbenzenesulfonamido)benzenesulfonyl]acrylonitrile: ##SPC31##

Workup

  1. stirringThe reaction mixture is stirred overnight
  2. filtrationfiltered
  3. additionthe filtrate diluted with 750 ml water
  4. filtrationwhich is recovered by filtration
  5. customdrying

Sources & evidence

ORD record
ord-073beb967e314a39a55a9b76c4a8bff5
Source dataset
uspto-grants-1976_03
Patent number
US03943154

Reaction notes

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