Acetic Anhydride → HCID 178516570, compound

HRID 1659104Notes

Reaction equation

HRID 1659104 reaction equation
[C:1]1([N:7]2[C:11](=[O:12])[CH2:10][S:9][C:8]2=[S:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[C:18](=[O:20])[CH3:19])(=O)C>>[OH:20][C:18](=[C:10]1[S:9][C:8](=[S:13])[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:11]1=[O:12])[CH2:19][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 738224-Thiazolidinone, 3-phenyl-2-thioxo-

Product 1

HCID 178516570HCID 178516570, compound

Procedure

A mixture of 25 g. (0.12 m.) of 3-phenylrhodanine, 80 g. (0.34 m.) of triethylorthophenylacetate [prepared as described in J.A.C.S. 68, 1917 (1946)] and 250 ml. of acetic anhydride is heated under reflux for 20 hours and the solution is then concentrated in vacuo. The residue is filtered and the solid is stirred with 160 ml. of dioxane, 160 ml. of water and 40 ml. of 10% sodium hydroxide for 4 hours. The solution is concentrated in vacuo at 35°-40°C. to evaporate the dioxane. The aqueous solution, after washing with ether and decolorizing with charcoal, is made acidic with dilute hydrochloric acid. The solid product is purified by chromatography to give 5-(1'-hydroxy-2'-phenylethylidene)-3-phenyl-rhodanine, m.p. 146-148°C.

Workup

  1. additionA mixture of 25 g
  2. custom(0.34 m.) of triethylorthophenylacetate [prepared as described in J.A.C.S. 68, 1917 (1946)] and 250 ml
  3. temperatureunder reflux for 20 hours
  4. concentrationthe solution is then concentrated in vacuo
  5. filtrationThe residue is filtered
  6. concentrationThe solution is concentrated in vacuo at 35°-40°C.
  7. customto evaporate the dioxane
  8. washThe aqueous solution, after washing with ether
  9. customThe solid product is purified by chromatography

Sources & evidence

ORD record
ord-152c369855534e3195cb28b1a3bd2ed2
Source dataset
uspto-grants-1976_06
Patent number
US03966942

Reaction notes

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