Sulfuric acid magnesium salt (1:1) → HCID 13934951, compound

HRID 2308906Notes

Reaction equation

HRID 2308906 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][NH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:4][C:3]=1[CH2:15][N:16]1[C:20](=[O:21])[C:19]([CH3:23])([CH3:22])[CH2:18][O:17]1.S([O-])([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1.[Ag]=O>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]=[N:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:4][C:3]=1[CH2:15][N:16]1[C:20](=[O:21])[C:19]([CH3:22])([CH3:23])[CH2:18][O:17]1

Participants

5

Reactant 2

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 13934964HCID 13934964, compound

Product 1

HCID 13934951HCID 13934951, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalyst2×HCID 1140TolueneSolvent

Procedure

A stirred mixture of 2-[[2-chloro-4-(ethoxycarbonylhydrazo)phenyl]methyl]-4,4-dimethyl-3-isoxazolidinone (1.24 g, 0.0036 mole) and magnesium sulfate (0.5 g, 0.004 mole) in toluene was cooled in a water bath. Silver oxide (0.6 g) was added and the mixture was stirred for one hour. Additional silver oxide (0.6 g) was added, and the mixture was stirred an additional one hour. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was chromatographed on silica gel, eluting first with 1:4 ethyl acetate:heptane and then 1:1 ethyl acetate:heptane. Appropriate fractions were combined and concentrated under reduced pressure to yield 1.0 g of 2-[[2-chloro-4-(ethoxycarbonylazo)phenyl]methyl]-4,4-dimethyl-3-isoxazolidinone as a red oil. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperaturewas cooled in a water bath
  2. stirringthe mixture was stirred an additional one hour
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was chromatographed on silica gel
  6. washeluting first with 1:4 ethyl acetate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-155de443ca1e465ca7154710ce4b6f8d
Source dataset
uspto-grants-1987_09
Patent number
US04692182

Reaction notes

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