Hydrochloric Acid → HCID 20043928, compound

HRID 1761318Notes

Reaction equation

HRID 1761318 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[CH2:11][O:10]2)=[C:4]([Cl:17])[CH:3]=1.Cl>CO>[ClH:17].[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13](=[O:14])[C:12]([CH3:15])([CH3:16])[CH2:11][O:10]2)=[C:4]([Cl:17])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 13557219HCID 13557219, compound

Product 1

HCID 20043928HCID 20043928, compoundYield 146%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.0 grams (0.008 mole) of 2-[(4-amino-2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone in 25 mL of methanol was stirred, and 0.78 gram (0.008 mole) of concentrated hydrochloric acid was added dropwise. Upon completion of addition the reaction mixture was stirred for 20 minutes. Analysis of the reaction mixture by thin layer chromatography (TLC) indicated the presence of unreacted amine. An additional 0.5 gram of concentrated hydrochloric acid was added, and the reaction mixture was stirred for 30 minutes more. The reaction mixture was concentrated under reduced pressure to a residue. The residue was dissolved in 20 mL of ethanol. A solid was precipitated from the solution by the addition of 20 mL of diethyl ether. The solid was collected by filtration and was dried to yield 1.7 grams of 2-[(4-amino-2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone hydrochloride as a solid.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. stirringthe reaction mixture was stirred for 30 minutes more
  3. concentrationThe reaction mixture was concentrated under reduced pressure to a residue
  4. dissolutionThe residue was dissolved in 20 mL of ethanol
  5. customA solid was precipitated from the solution by the addition of 20 mL of diethyl ether
  6. filtrationThe solid was collected by filtration
  7. customwas dried

Sources & evidence

ORD record
ord-91a5319e2f444893aa50258899d5885f
Source dataset
uspto-grants-1989_05
Patent number
US04826527

Reaction notes

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