Dimethyl Sulfoxide → HCID 14324546, compound

HRID 1460817Notes

Reaction equation

HRID 1460817 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.[C:20]1([C:26]2[O:30][N:29]=[CH:28][CH:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-:32].[K+].[K+]>O>[C:20]1([C:26]2[O:30][N:29]([C:2]3[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=3[N+:13]([O-:15])=[O:14])[C:28](=[O:32])[CH:27]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 136800Isoxazole, 5-phenyl-HCID 1268247Ethyl 4-chloro-3-nitrobenzoate

Product 1

HCID 14324546HCID 14324546, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After mixing 200 g of ethyl 4-chloro-3-nitrobenzoate, 500 ml of dimethyl sulfoxide, 169 g of 5-phenylisoxazole, and 146 g of potassium carbonate, the reaction was performed for 5 hours at 60° C. After the reaction was over, the reaction mixture was cooled and poured into water. Crystals thus deposited were recovered by filtration, washed with water, and dried to provide 292 g of the above-described compound with a yield of 94.6%. The melting point thereof was 142° C. to 143° C.

Workup

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

Sources & evidence

ORD record
ord-fd7714658d234b83a66e6f66dc6ea0ae
Source dataset
uspto-grants-1991_12
Patent number
US05071994

Reaction notes

Loading…