Methyl vinyl ketone → HCID 10856638, compound

HRID 1975623Notes

Reaction equation

HRID 1975623 reaction equation
[Cl:1][C:2]1[S:6][N:5]=[C:4]([OH:7])[CH:3]=1.[CH:8]([C:10]([CH3:12])=[O:11])=[CH2:9]>C1(C)C=CC=CC=1>[O:11]=[C:10]([CH3:12])[CH2:8][CH2:9][N:5]1[C:4](=[O:7])[CH:3]=[C:2]([Cl:1])[S:6]1

Participants

4

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 178516207HCID 178516207, compound

Product 1

HCID 10856638HCID 10856638, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 0.5 g (0.0037 mole) of 5-chloro-3-hydroxyisothiazole and methyl vinyl ketone (1.0 g, 0.014 mole) in 15 ml of toluene was heated at 80° C. for 24 hours. After cooling and removal of toluene and excess reagent by rotary evaporation, the residual oil was purified by column chromatography on silica gel, using diethyl ether/methanol (9/1) as eluant. Compound 1 was obtained as an oil; 0.65 g (85%); IR (neat) 1725,1650 cm-1 ; NMR (CDCl3) δ6.25 (s,1H); 4.0 (t,2H); 2.9 (t,2H); 2.2 (s,3H).

Workup

  1. temperatureAfter cooling
  2. customremoval of toluene and excess reagent
  3. customby rotary evaporation
  4. customthe residual oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-424a0a6c758242848448e6a0ed29185d
Source dataset
uspto-grants-1994_02
Patent number
US05288693

Reaction notes

Loading…