Dimethyl Sulfoxide → HCID 18707244, compound

HRID 263579Notes

Reaction equation

HRID 263579 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[C:15]([O:22][CH2:23][CH3:24])[CH:14]=3)[S:11][CH:12]=2)=[CH:4][C:3]=1[N+:25]([O-:27])=[O:26].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.CS(C)=O>CN(C)C=O>[O:31]1[CH2:32][CH2:33][N:28]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[N:9]=[C:10]([C:13]4[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[C:15]([O:22][CH2:23][CH3:24])[CH:14]=4)[S:11][CH:12]=3)=[CH:4][C:3]=2[N+:25]([O-:27])=[O:26])[CH2:29][CH2:30]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8083MorpholineHCID 18707279HCID 18707279, compound

Product 1

HCID 18707244HCID 18707244, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1 g of 4-(4-chloro-3-nitrophenyl)-2-(3,4-diethoxyphenyl)thiazole and 636 mg of morpholine dissolved in 20 ml of dimethylformamide and 20 ml of dimethyl sulfoxide was refluxed at 150° C. for 2-3.5 hours with heating. The reaction mixture was subjected to vacuum distillation. The residue was added to ice water, and an aqueous sodium hydrogencarbonate solution was added. The solution was extracted with dichloromethane three times. The combined extract was washed with an aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed by distillation. The residue was purified by silica gel column chromatography and recrystallized from ethyl acetate-n-hexane to obtain 1.03 g of 4-(4-morpholino-3-nitrophenyl)-2-(3,4-diethoxyphenyl)thiazole.

Workup

  1. temperaturewith heating
  2. distillationThe reaction mixture was subjected to vacuum distillation
  3. additionThe residue was added to ice water
  4. additionan aqueous sodium hydrogencarbonate solution was added
  5. extractionThe solution was extracted with dichloromethane three times
  6. extractionThe combined extract
  7. washwas washed with an aqueous sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was removed by distillation
  10. customThe residue was purified by silica gel column chromatography
  11. customrecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-e0bcfbb8b1504d0c928e6555f8712828
Source dataset
uspto-grants-1997_07
Patent number
US05643932

Reaction notes

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