Dimethyl Sulfoxide → HCID 14324510, compound

HRID 728526Notes

Reaction equation

HRID 728526 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].[C:16]([C:20]1[O:24][N:23]=[C:22]([OH:25])[CH:21]=1)([CH3:19])([CH3:18])[CH3:17].CS(C)=O.C(=O)(O)[O-].[Na+]>O.CO>[C:16]([C:20]1[O:24][N:23]([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:22](=[O:25])[CH:21]=1)([CH3:19])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 516892Sodium BicarbonateHCID 1268247Ethyl 4-chloro-3-nitrobenzoateHCID 178441207HCID 178441207, compound

Product 1

HCID 14324510HCID 14324510, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

413.3 g of ethyl 4-chloro-3-nitrobenzoate, 305 g of 5-t-butyl-3-hydroxyisooxazole and 1 liter of dimethyl sulfoxide were mixed, and stirred. Thereto was added 300 g of sodium bicarbonate, and the reaction was run at 90° C. for 8 hours. Thereafter, the reaction mixture was cooled, and thereto were added 1.5 liters of methanol, and further 3 liters of water to precipitate crystals. These crystals were filtered off. Yield: 560.7 g, Percent yield: 93.2%.

Workup

  1. temperatureThereafter, the reaction mixture was cooled
  2. customto precipitate crystals
  3. filtrationThese crystals were filtered off

Sources & evidence

ORD record
ord-7b2ff80c85d44b26b81637770c752f5e
Source dataset
uspto-grants-1991_09
Patent number
US05049477

Reaction notes

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