Triethylamine → 3-[4-(2,4,6-Trimethylbenzenesulfonamido)benzenesulfonyl]acrylonitrile

HRID 267583Notes

Reaction equation

HRID 267583 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10](Cl)(=[O:12])=[O:11].[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH:24]=[CH:25][C:26]#[N:27])(=[O:23])=[O:22])=[CH:17][CH:16]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10]([NH:14][C:15]1[CH:16]=[CH:17][C:18]([S:21]([CH:24]=[CH:25][C:26]#[N:27])(=[O:23])=[O:22])=[CH:19][CH:20]=1)(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chlorideHCID 545613262-Cyanovinyl 4-aminophenyl sulfone

Product 1

HCID 540421243-[4-(2,4,6-Trimethylbenzenesulfonamido)benzenesulfonyl]acrylonitrile

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 6.6 g (0.03 mol) of 2,4,6-trimethylbenzenesulfonyl chloride in 50 ml chloroform is added at room temperature to a stirred slurry of 6.3 g (0.03 mol) of 3-(4-aminobenzenesulfonyl)acrylonitrile in 100 ml chloroform, the slurry additionally containing 4 ml (0.03 mol) triethylamine, portionwise over a five minute period. After 3 hours stirring the reaction mixture is filtered. The chloroform solution is thereafter washed with water, dilute hydrochloric acid, and water, in that order, separated from the water layer, dried over anhydrous magnesium sulfate and evaporated. The recovered 3-[4-(2,4,6-trimethylbenzenesulfonamido)benzenesulfonyl]acrylonitrile has the formula: ##SPC18##

Workup

  1. filtrationis filtered
  2. washThe chloroform solution is thereafter washed with water, dilute hydrochloric acid, and water, in that order
  3. customseparated from the water layer
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-501b42157c7c48e993889e85ba5b34ea
Source dataset
uspto-grants-1976_03
Patent number
US03943154

Reaction notes

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