Acetic Acid → (2-Phenyl-4-thiazolyl)glyoxal

HRID 34739Notes

Reaction equation

HRID 34739 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[S:7][CH:8]=1)(=[O:3])[CH3:2].CC(O)=[O:17]>O>[C:9]1([C:6]2[S:7][CH:8]=[C:4]([C:1]([CH:2]=[O:17])=[O:3])[N:5]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 6048191-(2-Phenyl-1,3-thiazol-4-yl)ethan-1-one

Product 1

HCID 21298523(2-Phenyl-4-thiazolyl)glyoxal

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Acetyl-2-phenylthiazole (16.9 g., 0.083 mol) was dissolved in a mixture of 165 ml. CH3CO2H and 65 ml. H2O by warming to 50°. SeO2 (19.4 g., 0.175 mol) was added and the mixture refluxed for 3 hours, then decolorized with activated carbon, filtered, the filtrate concentrated to an oil, the residue taken up in 600 ml. ethyl acetate, washed 2×300 ml. saturated NaHCO3 and 1×300 ml. brine, and stripped to solids (crude hydrate), 16.2 g. The latter (6 g.) was heated to melting (155°) in vacuo for 10 minutes and cooled to yield title product as a glass; 1H-nmr 7.4-7.7 (m, 3H), 7.9-8.2 (m, 2H), 8.8 (s, 1H), 9.9 (s, 1H).

Workup

  1. temperaturethe mixture refluxed for 3 hours
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated to an oil
  4. washethyl acetate, washed 2×300 ml
  5. temperatureThe latter (6 g.) was heated
  6. custom(155°)
  7. customfor 10 minutes
  8. temperaturecooled

Sources & evidence

ORD record
ord-12dd6b14cc094ba59a5192a596f85079
Source dataset
uspto-grants-1988_08
Patent number
US04762921

Reaction notes

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