Acetic Acid → HCID 14324460, compound

HRID 1460814Notes

Reaction equation

HRID 1460814 reaction equation
C[CH:2]1O[N:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([O:15]CC)=[O:14])=[CH:9][C:8]=2[N+:18]([O-:20])=[O:19])[C:4](=[O:21])[CH2:3]1.[CH2:22]=[O:23].S(=O)(=O)(O)O.[ClH:29].[C:30](O)(=O)C>[Cl-].[Zn+2].[Cl-].O>[Cl:29][CH2:2][C:3]1[C:4](=[O:21])[N:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9][C:8]=2[N+:18]([O-:20])=[O:19])[O:23][C:22]=1[CH3:30]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric Acid2×HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 67924655HCID 67924655, compound

Product 1

HCID 14324460HCID 14324460, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent2×

Procedure

After mixing 279 g of 5-methyl-2-(4-ethoxycarbonyl-2-nitrophenyl)isoxazolin-3-one prepared in the above step, 700 ml of acetic acid, 129 g of paraformaldehyde, 156 g of zinc chloride, and 20 ml of sulfuric acid, the reaction system was saturated with hydrogen chloride gas at room temperature and the reaction was performed for 8 hours in a steam bath while further blowing hydrogen chloride gas into the system. Thereafter, 200 ml of water was added to the system and the reaction was further performed for 2 hours. After the reaction was over, the reaction mixture was cooled and then 2 liters of water was added thereto. Crystals thus deposited were recovered by filtration, washed with water, and dried to provide 199 g of the desired product with a yield of 66.7%. The melting point thereof was 190° C. to 191° C. (decompd.).

Workup

  1. temperaturewas cooled
  2. filtrationCrystals thus deposited were recovered by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-2cf9253642244653bc7d4223f226c4c5
Source dataset
uspto-grants-1991_12
Patent number
US05071994

Reaction notes

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