Hydrochloric Acid → 5-(5-Benzoyl-2-thienyl)oxazolidine-2,4-dione

HRID 1262937Notes

Reaction equation

HRID 1262937 reaction equation
[C:1]1([C:7]2([C:12]3[S:16][C:15]([CH:17]4[O:21][C:20](=[O:22])[NH:19][C:18]4=[O:23])=[CH:14][CH:13]=3)OCC[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCOCC.Cl>C(OCC)(=O)C>[C:7]([C:12]1[S:16][C:15]([CH:17]2[O:21][C:20](=[O:22])[NH:19][C:18]2=[O:23])=[CH:14][CH:13]=1)(=[O:8])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 129626755-[5-(2-Phenyl-1,3-dioxolan-2-yl)-2-thienyl]-oxazolidine-2,4-dione

Product 1

HCID 129626765-(5-Benzoyl-2-thienyl)oxazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-[5-(2-Phenyl-1,3-dioxolan-2-yl)-2-thienyl]-oxazolidine-2,4-dione (0.40 g.) was dissolved in 30 ml. of ether and stirred with 10 ml. of 6 N hydrochloric acid at room temperature for 1 hour. Ethyl acetate (10 ml.) was added, and the organic layer was separated and evaporated in vacuo to dryness (0.388 g.). Chromatography on 50 ml. of silica gel, eluted with 1:1 hexane:ethyl acetate/5% acetic acid and monitored by tlc, gave in early fractions purified 5-(5-benzoyl-2-thienyl)oxazolidine-2,4-dione (0.22 g., m.p. 153°-155° C., m/e 287).

Workup

  1. customthe organic layer was separated
  2. customevaporated in vacuo to dryness (0.388 g.)
  3. washof silica gel, eluted with 1:1 hexane
  4. customgave in early fractions
  5. custompurified 5-(5-benzoyl-2-thienyl)oxazolidine-2,4-dione (0.22 g., m.p. 153°-155° C., m/e 287)

Sources & evidence

ORD record
ord-a86961dcac2c4cb3af65becec8a89bc3
Source dataset
uspto-grants-1984_06
Patent number
US04454320

Reaction notes

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