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

HRID 1975627Notes

Reaction equation

HRID 1975627 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-2801c3c5167e488e8a6514271d990a3f
Source dataset
uspto-grants-1994_02
Patent number
US05288693

Reaction notes

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