Water → HCID 70373300, compound

HRID 329564Notes

Reaction equation

HRID 329564 reaction equation
[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[C:22](=[O:23])[C:21]([CH3:25])([CH3:24])[CH2:20][O:19]2)=[C:13]([Cl:26])[CH:12]=1.O>C(O)C>[Cl:26][C:13]1[CH2:12][C:11](=[N:10][CH2:1][C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[OH:4])[CH:16]=[CH:15][C:14]=1[CH2:17][N:18]1[C:22](=[O:23])[C:21]([CH3:25])([CH3:24])[CH2:20][O:19]1

Participants

5

Reactant 3

HCID 962WaterHCID 6998SalicylaldehydeHCID 13557219HCID 13557219, compound

Product 1

HCID 70373300HCID 70373300, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A warmed solution of 0.48 gram (0.004 mole) of salicylaldehyde in 35 mL of ethanol was stirred, and 1.0 gram (0.004 mole) of 2-[(4-amino-2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone was added in one portion. The reaction mixture was heated an additional 30 minutes and then 15 mL of water was added. The mixture was filtered, and the filtrate was cooled. The resultant oily suspension solidified when abraded. The solid was collected by filtration to yield, when dried, 0.87 gram of 2-[[2-chloro-4-[(2-hydroxyphenyl)methylimino]phenyl]-methyl]-4,4-dimethyl-3-isoxazolidinone; m.p. 105°-107° C.

Workup

  1. temperatureThe reaction mixture was heated an additional 30 minutes
  2. filtrationThe mixture was filtered
  3. temperaturethe filtrate was cooled
  4. filtrationThe solid was collected by filtration
  5. customto yield
  6. customwhen dried

Sources & evidence

ORD record
ord-9815d93ad8334a90b730bb34696b8999
Source dataset
uspto-grants-1990_01
Patent number
US04892578

Reaction notes

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