Benzosulfinide sodium; Garantose sodium → HCID 54235115, compound

HRID 1284538Notes

Reaction equation

HRID 1284538 reaction equation
[C:1]([C:3](=[CH:5][CH2:6]Cl)[CH3:4])#[N:2].[S:8]1([C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:12](=[O:13])[NH:11]1)(=[O:10])=[O:9].[Na]>CN(C)C=O>[O:10]=[S:8]1(=[O:9])[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:12](=[O:13])[N:11]1[CH2:6][CH:5]=[C:3]([C:1]#[N:2])[CH3:4]

Participants

4

Reactant 2

HCID 24181110Benzosulfinide sodium; Garantose sodiumHCID 54181059HCID 54181059, compound

Product 1

HCID 54235115HCID 54235115, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

18.2 g (150 millimoles) of 2-cyano-4-chlorobut-2-ene were slowly added dropwise to 20.0 g (100 millimoles) of sodium saccharin in 100 ml of absolute dimethylformamide, while stirring thoroughly. The reaction mixture was stirred for a further 4 hours at 40° C., after which the precipitated sodium chloride was filtered off and the filtrate was evaporated down under reduced pressure to about 30 ml. After 400 ml of water had been added, the oil initially formed slowly crystallized. The crystals were filtered off under suction, recrystallized from ethanol and dried in a drying oven under reduced pressure at 50° C. to give 17.4 g (66%) of 4-(2,3-dihydro-1,1-dioxido-3-oxo-1,2-benzisothiazol-2-yl)-2-cyanobut-2-ene of melting point 107°-108° C.

Workup

  1. stirringThe reaction mixture was stirred for a further 4 hours at 40° C.
  2. filtrationafter which the precipitated sodium chloride was filtered off
  3. customthe filtrate was evaporated down under reduced pressure to about 30 ml
  4. additionAfter 400 ml of water had been added
  5. customthe oil initially formed slowly
  6. customcrystallized
  7. filtrationThe crystals were filtered off under suction
  8. customrecrystallized from ethanol
  9. customdried in a drying oven under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-4c4b4e1a3d4c4378b0a6e5ae72832de0
Source dataset
uspto-grants-1986_01
Patent number
US04563474

Reaction notes

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