Dabco → HCID 54410119, compound

HRID 267591Notes

Reaction equation

HRID 267591 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][S:16]([C:19]1[CH:20]=[C:21]([S:25](Cl)(=[O:27])=[O:26])[CH:22]=[CH:23][CH:24]=1)(=[O:18])=[O:17].S(Cl)(Cl)(=O)=O.N12CCN(CC1)CC2>CC(C)=O>[F:15][S:16]([C:19]1[CH:20]=[C:21]([S:25]([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:27])=[O:26])[CH:22]=[CH:23][CH:24]=1)(=[O:17])=[O:18]

Participants

6

Reactant 4

HCID 9237DabcoHCID 24648Sulfuryl chlorideHCID 75603Benzenesulfonyl fluoride, 3-(chlorosulfonyl)-HCID 545613262-Cyanovinyl 4-aminophenyl sulfone

Product 1

HCID 54410119HCID 54410119, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
25 °C

Procedure

To an acetone solution of 10.4 g (0.05 mol) 2-cyanovinyl 4-aminophenyl sulfone is added 12.8 g (0.05 mol of 3-fluorosulfonylbenzenesulfonyl chloride at room temperature, with agitation. The sulfonyl chloride dissolves immediately, giving a clear yellow solution. To this mixture is added over a ten minute period an acetone solution of 1,4-diazabicyclo[2.2.2]-octane (11.2 g, 0.05 mol). A light yellow precipitate forms almost at once; the reaction mixture is maintained at about 25° C for 30 minutes with stirring. Precipitation in water and workup affords a bright yellow powder, 2-cyanovinyl 4-(3-fluorosulfonylbenzenesulfonamido)phenyl sulfone: ##SPC44##

Workup

  1. customgiving a clear yellow solution
  2. customPrecipitation in water

Sources & evidence

ORD record
ord-a2723df0638d4742995091f7c46cb9f3
Source dataset
uspto-grants-1976_03
Patent number
US03943154

Reaction notes

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