Hydrochloric Acid → HCID 19966768, compound

HRID 976227Notes

Reaction equation

HRID 976227 reaction equation
[CH3:1][CH:2]([O:5][C:6]1[C:7]([Cl:16])=[CH:8][C:9]([F:15])=[C:10]([N:12]=[C:13]=[O:14])[CH:11]=1)[C:3]#[CH:4].C([N:19]([CH2:22][CH3:23])CC)C.[CH:24](OC(C)C)([CH3:26])[CH3:25].Cl.C(OCC)(=[O:34])C>C(OCC)C>[CH3:1][CH:2]([O:5][C:6]1[C:7]([Cl:16])=[CH:8][C:9]([F:15])=[C:10]([N:12]2[C:22](=[NH:19])[C:23](=[C:24]([CH3:26])[CH3:25])[O:14][C:13]2=[O:34])[CH:11]=1)[C:3]#[CH:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 54115859HCID 54115859, compound

Product 1

HCID 19966768HCID 19966768, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A round-bottomed flask (300 cc) equipped with a dropping funnel was charged with 5-(1-methyl-2-propynyloxy)-4-chloro-2-fluorophenyl isocyanate (10.0 g, 41.7 mmol) and triethylamine (1.0 mL), as well as isopropyl ether (40 mL) and diethyl ether (50 mL) and methacrolein cyanohydrin (4.86 g, 50.0 mmol) was dropwise added slowly with stirring under cooling in an ice-water bath. After the addition, the mixture was heated to room temperature and stirred for an additional 12 h. After completion of the reaction, the reaction mixture was poured into 1N HCl (50 mL) and extraction was conducted with ethyl acetate (50 mL×3). The organic layer was dried with magnesium sulfate and the solvent was subsequently distilled off under vacuum to yield a crude product, which was purified by silica gel column chromatography (eluting solvents: ethyl acetate/hexane=1/5). The separated product of interest in turn was recrystallized from ether/hexane to give 3-[5-(1-methyl-2-propynyloxy)-4-chloro-2-fluorophenyl]-4-imino-5-isopropylideneoxazolidine-2-one (compound 5) as a white crystal (7.37 g; yield, 52.4%).

Workup

  1. customA round-bottomed flask (300 cc) equipped with a dropping funnel
  2. temperatureunder cooling in an ice-water bath
  3. additionAfter the addition
  4. stirringstirred for an additional 12 h
  5. customAfter completion of the reaction
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. distillationthe solvent was subsequently distilled off under vacuum
  8. customto yield a crude product, which
  9. customwas purified by silica gel column chromatography (eluting solvents: ethyl acetate/hexane=1/5)
  10. customThe separated product of interest in turn was recrystallized from ether/hexane
  11. customto give

Sources & evidence

ORD record
ord-d63f1c4955674db987869f05c2c53740
Source dataset
uspto-grants-1997_03
Patent number
US05612289

Reaction notes

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