Dimethyl Sulfoxide → HCID 14324515, compound

HRID 1588390Notes

Reaction equation

HRID 1588390 reaction equation
Cl[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].CS(C)=O.[CH3:20][C:21]1[O:25][N:24]=[C:23]([OH:26])[CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:20][C:21]1[O:25][N:24]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=2[N+:13]([O-:15])=[O:14])[C:23](=[O:26])[CH:22]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 24781HymexazolHCID 1268247Ethyl 4-chloro-3-nitrobenzoate

Product 1

HCID 14324515HCID 14324515, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After mixing 400 g of ethyl 4-chloro-3-nitrobenzoate, 1.2 liters of dimethyl sulfoxide, 270 g of 5-methyl-3-hydroxyisoxazole, and 292 g of potassium carbonate, the reaction was performed for 10 hours at 60° C. After the reaction was over, the reaction mixture was poured into water and crystals thus deposited were recovered by filtration and recrystallized from ethyl acetate to provide 300.1 g of the desired compound with a yield of 59.0%. The melting point thereof was 122° C. to 123° C.

Workup

  1. filtrationthus deposited were recovered by filtration
  2. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a1fe63d8af234b769e90dd900e3cecb1
Source dataset
uspto-grants-1993_06
Patent number
US05221750

Reaction notes

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