Ammonium Chloride → HCID 18353681, compound

HRID 430072Notes

Reaction equation

HRID 430072 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([CH:15]2[NH:18][C:17](=O)[CH2:16]2)[CH:11]=[CH:12][C:13]=1[Cl:14].[Cl-].[NH4+]>C(OCC)C>[Cl:7][C:8]1[CH:9]=[C:10]([CH:15]2[CH2:16][CH2:17][NH:18]2)[CH:11]=[CH:12][C:13]=1[Cl:14]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 183537284-(3,4-Dichlorophenyl)azetidin-2-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 18353681HCID 18353681, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To lithium aluminium hydride (0.63 g, 16.5 mmol) in diethyl ether (12 ml) was added 4-(3,4-dichlorophenyl)azetidin-2-one (1 g, 4.6 mmol). The mixture was refluxed under argon for 4 h then cooled and 20% aqueous ammonium chloride solution (3 ml) added. Diethyl ether (30 ml) was added and the mixture filtered, and the insoluble material washed with more diethyl ether (20 ml). The combined filtrates were dried (Na2SO4) and evaporated under reduced pressure to give a yellow oil, (0.76 g). A portion of this material (0.55 g) was purified by column chromatography on silica gel eluting with 2-10% (9:1 MeOH/0.880 NH3) in dichloromethane gave the title compound, (0.44 g, 65%). δH (CDCl3) 2.0 (1H, bs), 2.3 (1H, m), 2.55 (1H, m), 3.34 (1h, m), 3.75 (1H, m), 4.9(1H, t), 7.2 (1H, dd), 7.4(1H, d), 7.5 (1H, d).

Workup

  1. temperatureThe mixture was refluxed under argon for 4 h
  2. temperaturethen cooled
  3. filtrationthe mixture filtered
  4. washthe insoluble material washed with more diethyl ether (20 ml)
  5. dry with materialThe combined filtrates were dried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customto give a yellow oil, (0.76 g)
  8. customA portion of this material (0.55 g) was purified by column chromatography on silica gel eluting with 2-10% (9:1 MeOH/0.880 NH3) in dichloromethane

Sources & evidence

ORD record
ord-d87144df5e914e16bced0e362cb2d32f
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

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