HCID 54363480, compound → HCID 13321926, compound

HRID 1284541Notes

Reaction equation

HRID 1284541 reaction equation
[O:1]=[S:2]1(=[O:18])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])[N:3]1[CH2:12][C:13]([CH3:17])=[CH:14][C:15]#[N:16]>C(O)C.CN(C)C=O.[Pd]>[O:1]=[S:2]1(=[O:18])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])[N:3]1[CH2:12][CH:13]([CH3:17])[CH2:14][C:15]#[N:16]

Participants

5

Reactant 1

HCID 54363480HCID 54363480, compound

Product 1

HCID 13321926HCID 13321926, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

10.0 g (38 millimoles) of 3-(2,3-dihydro-1,1-dioxido-3-oxo-1,2-benzisothiazol-2-yl)-1-cyano-2-methylprop-1-ene (Example 1) were dissolved in 200 ml of ethanol and 100 ml of dimethylformamide, 1 g of palladium on active carbon (10%) was added and hydrogenation was carried out for 12 hours at room temperature and under atmospheric pressure. The mixture was filtered, the filtrate was evaporated down under reduced pressure and the resulting greenish oil was purified by column chromatography (silica gel, mobile phase 85:15 mixture of toluene and methanol) to give 4.8 g (48%) of 3-(2,3-dihydro-1,1-dioxido-3-oxo-1,2-benzisothiazol-2-yl)-1-cyano-2-methylpropane in the form of an oil which slowly crystallized through. Mp 83°-84° C.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated down under reduced pressure
  3. customthe resulting greenish oil was purified by column chromatography (silica gel, mobile phase 85:15 mixture of toluene and methanol)

Sources & evidence

ORD record
ord-9a60902eb63049958c786cf5fce1d858
Source dataset
uspto-grants-1986_01
Patent number
US04563474

Reaction notes

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