Dabco → HCID 68140610, compound

HRID 267592Notes

Reaction equation

HRID 267592 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([S:7](Cl)=[O:8])=[CH:3][CH:2]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH:21]=[CH:22][C:23]#[N:24])(=[O:20])=[O:19])=[CH:14][CH:13]=1.N12CCN(CC1)CC2>CC(C)=O>[CH3:10][C:1]1[CH:6]=[CH:5][C:4]([S:7]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([S:18]([CH:21]=[CH:22][C:23]#[N:24])(=[O:20])=[O:19])=[CH:16][CH:17]=2)=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 41900044-methylbenzenesulfinyl chlorideHCID 545613262-Cyanovinyl 4-aminophenyl sulfone

Product 1

HCID 68140610HCID 68140610, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

17.5 g p-toluenesulfinyl chloride (obtained by treating sodium toluenesulfinate.2H2O with thionyl chloride) is dissolved in 100 ml of acetone and this solution is added at room temperature and with stirring to a solution of 20.8 g (0.1 mol) of 2-cyanovinyl 4-aminophenyl sulfone in 250 ml of acetone. Shortly thereafter a solution of 11.2 g (0.1 mol) of 1,4-diazabicyclo[2.2.2]octane in 150 ml of acetone is added over about 10 minutes and the reaction mixture is stirred for another 20 minutes. The reaction mixture is filtered, evaporated in air to about a third of its volume, and then poured into cold water. The precipitate is filtered, washed and dried to give 3-[4-(4-methylbenzenesulfinamido)benzenesulfonyl]acrylonitrile: ##SPC45##

Workup

  1. additionthis solution is added at room temperature
  2. filtrationThe reaction mixture is filtered
  3. customevaporated in air to about a third of its volume
  4. additionpoured into cold water
  5. filtrationThe precipitate is filtered
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-47a1697a1e5648b68c6e652a38023d48
Source dataset
uspto-grants-1976_03
Patent number
US03943154

Reaction notes

Loading…