Acetonitrile → HCID 57105078, compound

HRID 619892Notes

Reaction equation

HRID 619892 reaction equation
C(#N)C.[Cl:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([OH:12])=[CH:7][C:6]=1[N:13]1[C:17](=[O:18])[C:16](=[C:19]([CH2:21][CH3:22])[CH3:20])[O:15][C:14]1=[O:23].C(=O)([O-])[O-].[K+].[K+].Br[CH:31]([CH3:37])[C:32]([O:34][CH2:35][CH3:36])=[O:33]>CCOCC>[Cl:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][CH:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH3:37])=[CH:7][C:6]=1[N:13]1[C:17](=[O:18])[C:16](=[C:19]([CH2:21][CH3:22])[CH3:20])[O:15][C:14]1=[O:23]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 57282696HCID 57282696, compound

Product 1

HCID 57105078HCID 57105078, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To an acetonitrile solution (30 ml) of a mixture of 3-(2',4'-dichloro-5'-hydroxyphenyl)-5-(sec-butylidene)-1,3-oxazolidine-2,4-dione (1.58 g, 5 mmol) was added potassium carbonate (0.69 g), and the mixture was heated at reflux for 2 hours. After the addition of ethyl 2-bromopropionate (0.93 g, 5.1 mmol), the reaction mixture was further refluxed for 1 hour. Ether was added to the reaction mixture and the solution was washed with 1N hydrochloric acid and extracted with ether. The ethereal extracts combined were dried and then evaporated as small a volume as possible. The resulting residue was purified by silica gel column chromatography to give 3-{2',4'-dichloro-5'-(1"-ethoxycarbonylethyloxy)phenyl}-5-(sec-butylidene)-1,3-oxazolidine-2,4-dione. (1.51 g, 73% yield)

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperaturethe reaction mixture was further refluxed for 1 hour
  4. washthe solution was washed with 1N hydrochloric acid
  5. extractionextracted with ether
  6. customThe ethereal extracts combined were dried
  7. customevaporated as small a volume as possible
  8. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-68776595c1ad42fdb21f3418c562b708
Source dataset
uspto-grants-1989_04
Patent number
US04818272

Reaction notes

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