Hydrochloric Acid → HCID 13557219, compound

HRID 1761317Notes

Reaction equation

HRID 1761317 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8]C(OCC)=O)[CH:5]=[CH:4][C:3]=1[CH2:14][N:15]1[C:19](=[O:20])[C:18]([CH3:22])([CH3:21])[CH2:17][O:16]1.I[Si](C)(C)C.Cl>C(Cl)(Cl)Cl>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:14][N:15]2[C:19](=[O:20])[C:18]([CH3:21])([CH3:22])[CH2:17][O:16]2)=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 85247Trimethylsilyl iodideHCID 13557218HCID 13557218, compound

Product 1

HCID 13557219HCID 13557219, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2.0 grams (0.006 mole) of 2-[[2-chloro-4-(ethoxycarbonylamino)phenyl]methyl]-4,4-dimethyl-3-isoxazolidinone in 20 mL of chloroform was stirred under an argon atmosphere, and 1.1 mL (0.007 mole) of iodotrimethylsilane was added via syringe. The reaction mixture was heated to 60° C. where it was stirred for two hours. After this time the reaction mixture was warmed to 70° C. where it was stirred for 16 hours. The reaction mixture was cooled to ambient temperature, and 10 mL of methanolic 2N hydrochloric acid was added. The resultant clear solution was concentrated under reduced pressure, and the residue was slurried in 50 mL of water. An insoluble material was removed by filtration, and the filtrate was neutralized with an aqueous solution saturated with sodium bicarbonate. The mixture was extracted with methylene chloride, and the combined extracts were dried with magnesium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure to a solid residue. The solid was recrystallized from hexane-ethyl acetate to yield 0.4 gram of 2-[(4-amino-2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone; m.p. 105°-107° C.

Workup

  1. stirringwas stirred for two hours
  2. temperatureAfter this time the reaction mixture was warmed to 70° C. where it
  3. stirringwas stirred for 16 hours
  4. temperatureThe reaction mixture was cooled to ambient temperature
  5. concentrationThe resultant clear solution was concentrated under reduced pressure
  6. customAn insoluble material was removed by filtration
  7. extractionThe mixture was extracted with methylene chloride
  8. dry with materialthe combined extracts were dried with magnesium sulfate
  9. filtrationThe mixture was filtered
  10. concentrationthe filtrate was concentrated under reduced pressure to a solid residue
  11. customThe solid was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-ef438005ead246c4b06c771e61342a35
Source dataset
uspto-grants-1989_05
Patent number
US04826527

Reaction notes

Loading…