Hydrochloric Acid → 2-([4-[2-(4-Methanesulfonyloxyphenyl)ethoxy]phenyl]methyl) 1,2,4-oxadiazolidine-3,5-dione

HRID 1595525Notes

Reaction equation

HRID 1595525 reaction equation
[C:1](=[O:6])=[N:2][C:3](Cl)=[O:4].[CH3:7][S:8]([O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][NH:28][OH:29])=[CH:23][CH:22]=2)=[CH:14][CH:13]=1)(=[O:10])=[O:9].Cl>O1CCCC1>[CH3:7][S:8]([O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][O:20][C:21]2[CH:22]=[CH:23][C:24]([CH2:27][N:28]3[C:3](=[O:4])[NH:2][C:1](=[O:6])[O:29]3)=[CH:25][CH:26]=2)=[CH:14][CH:13]=1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 119708Isocyanatocarbonyl chlorideHCID 217049544-(2-{4-[Hydroxyaminomethyl]phenoxy}ethyl)phenyl methanesulfonate

Product 1

HCID 882341712-([4-[2-(4-Methanesulfonyloxyphenyl)ethoxy]phenyl]methyl) 1,2,4-oxadiazolidine-3,5-dioneYield 15.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

0.45 g (4 mmole) N-(chlorocarbonyl)isocyanate was added dropwise to a solution of 1.2 g (3.6 ml) 4-(2-{4-[hydroxyaminomethyl]phenoxy}ethyl)phenyl methanesulfonate in 20 ml anhydrous tetrahydrofuran at −5° C. and the mixture was stirred at −5° C. for 30 minutes. The reaction mixture was poured on to 2 M hydrochloric acid and extracted with ethyl acetate, dried (sodium sulfate), filtered and evaporated in vacuo. The residue was redissolved in ethyl acetate, and material that did not go into solution was filtered off. The filtrate was evaporated in vacuo, diethyl ether was added to give a white precipitate which was filtered off and recrystallized in diethyl ether/acetone to give 0.223 g of the desired product. The mother liquid was evaporated in vacuo and purified by chromatography on silica gel using dichloromethane:methanol (95:5) as eluent and crystallized in diethyl ether to give 0.09 g more of the desired product (total yield 0.384 g, 26.2%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (sodium sulfate)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. dissolutionThe residue was redissolved in ethyl acetate
  6. filtrationwas filtered off
  7. customThe filtrate was evaporated in vacuo, diethyl ether
  8. additionwas added
  9. customto give a white precipitate which
  10. filtrationwas filtered off
  11. customrecrystallized in diethyl ether/acetone

Sources & evidence

ORD record
ord-7f003ba288fa44b08e5b02e16743685d
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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