Sulfuric Acid → 4-Chloromethyl-5-phenyl-2-(4-carboxy-2-nitrophenyl)-4-isoxazolin-3-one

HRID 1460819Notes

Reaction equation

HRID 1460819 reaction equation
S(=O)(=O)(O)O.[Cl:6][CH2:7][C:8]1[C:9](=[O:33])[N:10]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27]CC)=[O:26])=[CH:21][C:20]=2[N+:30]([O-:32])=[O:31])[O:11][C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O1CCOCC1>O>[Cl:6][CH2:7][C:8]1[C:9](=[O:33])[N:10]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[CH:21][C:20]=2[N+:30]([O-:32])=[O:31])[O:11][C:12]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 312751,4-DioxaneHCID 14324463HCID 14324463, compound2×

Product 1

HCID 199825024-Chloromethyl-5-phenyl-2-(4-carboxy-2-nitrophenyl)-4-isoxazolin-3-oneYield 83.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After adding 300 ml of concentrated sulfuric acid to a mixture of 270 g (0.67) of 4-chloromethyl-5-phenyl-2-(4-ethoxycarbonyl-2-nitrophenyl)-4-isoxazolin-3-one (Compound (33)) and 2.5 liters of 1,4-dioxane, the resultant mixture was refluxed for 8 hours. Thereafter, the reaction mixture obtained was cooled and poured into water. Crystals thus deposited were recovered by filtration, washed with water, and dried to provide 210.2 g of the aforesaid compound with a yield of 83.7%. The melting point thereof was 186° C. to 189° C.

Workup

  1. customThereafter, the reaction mixture obtained
  2. temperaturewas cooled
  3. filtrationCrystals thus deposited were recovered by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-e8756ad4d04b4b50b788dec741b4fc88
Source dataset
uspto-grants-1991_12
Patent number
US05071994

Reaction notes

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