2-Acryloyl-1,4-benzoquinone → HCID 19021013, compound

HRID 1109616Notes

Reaction equation

HRID 1109616 reaction equation
[C:1]([C:5]1[C:6](=[O:12])[CH:7]=[CH:8][C:9](=[O:11])[CH:10]=1)(=[O:4])[CH:2]=[CH2:3].[Cl:13][C:14]1[S:18][N:17]=[C:16]([OH:19])[CH:15]=1>C1(C)C=CC=CC=1>[Cl:13][C:14]1[S:18][N:17]([CH2:3][CH2:2][C:1]([C:5]2[C:6](=[O:12])[CH:7]=[CH:8][C:9](=[O:11])[CH:10]=2)=[O:4])[C:16](=[O:19])[CH:15]=1

Participants

4

Reactant 2

HCID 190210272-Acryloyl-1,4-benzoquinoneHCID 178516207HCID 178516207, compound

Product 1

HCID 19021013HCID 19021013, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 2-acryloyl-1,4-benzoquinone (1.0 g, 0.007 mole) and 5-chloro-3-hydroxyisothiazole (0.81 g, 0.006 mole) in 20 ml of toluene was heated at 80° C. for 4 hours. Upon cooling, the precipitate which formed during the reaction period was removed by filtration and recrystallized from ethyl acetate/acetone mixture. A gray/tan solid was obtained; 0.85 g; mp 181°-183° C.; IR (KBR) 1635 cm-1 (broad); NMR (acetone-d6) δ7.35 (s, 1H); 7.15 (d, 1H); 6.85 (d, 1H); 6.35 (s, 1H); 4.2 (t, 2H); 3.52 (t, 2H).

Workup

  1. temperatureUpon cooling
  2. customthe precipitate which formed during the reaction period
  3. customwas removed by filtration
  4. customrecrystallized from ethyl acetate/acetone mixture
  5. customA gray/tan solid was obtained

Sources & evidence

ORD record
ord-b1fddadad41747ecae5031fb2a4aa8e8
Source dataset
uspto-grants-1994_06
Patent number
US05321141

Reaction notes

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