Water → HCID 13423443, compound

HRID 2164403Notes

Reaction equation

HRID 2164403 reaction equation
[CH3:1][C:2]1[NH:3][O:4][C:5](=[O:7])[CH:6]=1.N1C=CC=CC=1.[N+:14]([C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1)([O-:16])=[O:15].O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:3]([C:21](=[O:22])[C:20]2[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:25][CH:24]=2)[O:4][C:5](=[O:7])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 85024-Nitrobenzoyl chlorideHCID 1530003-Methylisoxazol-5-one

Product 1

HCID 13423443HCID 13423443, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

4 gm of 3-methyl-3-isoxazolin-5-one was added to 20 ml of toluene along with 3.5 gm of pyridine. 8.2 gm of 4-nitrobenzoyl chloride in 80 ml of toluene was added dropwise. The solution was stirred at room temperature for 4 hours. Afterwards, the system was poured into 200 ml water. The resulting solution was filtered and the organic phase then separated and dried over sodium sulfate. The toluene was removed by stripping to give 6.9 gm of a mixture of 3-methyl-2-(4'-nitrobenzoyl)-3-isoxazolin-5-one and 3-methyl-5-hydroxyisoxazolyl4'-nitrobenzoate. The crude product was recrystallized in ethanol to give 4.6 gm of the mixture. The product 3-methyl-2-(4-nitrobenzoyl)-3-isoxazolin-5-one was separated by column chromatography using 200 gm of E.M. silica gel 60 in an 80×90 mm column and a 2% solution of acetone in methylene chloride as the elutant. Listed as compound number 1, Table I.

Workup

  1. filtrationThe resulting solution was filtered
  2. customthe organic phase then separated
  3. dry with materialdried over sodium sulfate
  4. customThe toluene was removed

Sources & evidence

ORD record
ord-50851eda8f3a4e18a23fe57935d41056
Source dataset
uspto-grants-1985_03
Patent number
US04504486

Reaction notes

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