p-Toluenesulfonic acid → 2-(2-Oxo-3-buten-4-yl)-5-chloro-4-isothiazolin-3-one

HRID 1109617Notes

Reaction equation

HRID 1109617 reaction equation
[Cl:1][C:2]1[S:6][N:5]=[C:4]([OH:7])[CH:3]=1.[CH:8]#[C:9][C:10](=[O:12])[CH3:11].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:12]=[C:10]([CH:9]=[CH:8][N:5]1[C:4](=[O:7])[CH:3]=[C:2]([Cl:1])[S:6]1)[CH3:11]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 15018Butyn-2-oneHCID 178516207HCID 178516207, compound

Product 1

HCID 541736702-(2-Oxo-3-buten-4-yl)-5-chloro-4-isothiazolin-3-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 5-chloro-3-hydroxyisothiazole (1.5 g, 0.011 mole), 1-butyn-3-one (3.5 g, 0.05 mole) and p-toluenesulfonic acid (0.02 g) in 25 ml of toluene was heated at 80° C. for 24 hours. Upon cooling, the dark brown reaction mixture was concentrated and the residual oil was column chromatographed on silica gel, using diethyl ether/hexane as eluant. Compound 11 was obtained as a yellowish solid; 1.8 g; mp 137°-139° C.; IR (KBr) 1675, 1620 cm-1 ; NMR (CDCl3) δ8.2 (d, 1H, J=13.9 Hz); 6.35 (s, 1H); 5.85 (d, 1H, J=13.9 Hz); 2.35 (s, 3H).

Workup

  1. temperatureUpon cooling
  2. concentrationthe dark brown reaction mixture was concentrated
  3. customchromatographed on silica gel

Sources & evidence

ORD record
ord-0844a9bf338e40fe9d5274f6f5e6fb11
Source dataset
uspto-grants-1994_06
Patent number
US05321141

Reaction notes

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