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

HRID 267585Notes

Reaction equation

HRID 267585 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.[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.C(N(CCCC)CCCC)CCC.O>CC(C)=O>[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([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:24])=[O:23])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7622TributylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 545613262-Cyanovinyl 4-aminophenyl sulfone

Product 1

HCID 540732553-[4-(4-Fluorobenzenesulfonamido)benzenesulfonyl]acrylonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

24 g (0.12 mol) of 3-(4-aminobenzenesulfonyl)acrylonitrile are dissolved in 200 ml acetone. 23.4 g (0.12 mol) of a solution of p-fluorobenzenesulfonyl chloride in 100 ml acetone are added thereto in several portions at room temperature, followed by 28 ml (0.12 mol) tributylamine. After standing for 8 hours at room temperature the reaction mixture is poured into 1 liter of water to separate the reaction product, which is then taken up in chloroform, and treated as described hereinabove to give 3-[4-(4-fluorobenzenesulfonamido)benzenesulfonyl]acrylonitrile: ##SPC21##

Workup

  1. customat room temperature
  2. customto separate the reaction product, which
  3. additiontreated

Sources & evidence

ORD record
ord-18b0b5d1426e45bf8dab7c4f2f577fd8
Source dataset
uspto-grants-1976_03
Patent number
US03943154

Reaction notes

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