Hydroquinone → HCID 10856638, compound

HRID 1109611Notes

Reaction equation

HRID 1109611 reaction equation
[Cl:1][C:2]1[S:6][N:5]=[C:4]([OH:7])[CH:3]=1.[C:8]1([CH:15]=CC(O)=[CH:11][CH:10]=1)[OH:9]>C1(C)C=CC=CC=1>[O:9]=[C:8]([CH3:15])[CH2:10][CH2:11][N:5]1[C:4](=[O:7])[CH:3]=[C:2]([Cl:1])[S:6]1

Participants

4

Reactant 2

HCID 785HydroquinoneHCID 178516207HCID 178516207, compound

Product 1

HCID 10856638HCID 10856638, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-chloro-3-hydroxyisothiazole (1.5 g, 0.011 mole), 2-trimethylysiloxy-1,3-butadiene (5.6 g, 0.04 mole) and 0.5 g of hydroquinone in 20 ml of toluene was heated at 80° C. for 96 hours. After cooling, the mixture was concentrated in vacuo. The residual oil was dissolved in diethyl ether and washed with saturated NaHCO3 solution and then with water. After drying (MgSO4) and concentrating the solution, 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, 0.3 g; IR (neat) 1625, 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. concentrationthe mixture was concentrated in vacuo
  3. dissolutionThe residual oil was dissolved in diethyl ether
  4. washwashed with saturated NaHCO3 solution
  5. dry with materialAfter drying (MgSO4)
  6. concentrationconcentrating the solution
  7. customthe residual oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0aae3469271b47f98cd6f28d946674ff
Source dataset
uspto-grants-1994_06
Patent number
US05321141

Reaction notes

Loading…