Dimethyl Sulfoxide → 5-(3,4-Dimethoxyphenyl)-2-oxazolidinethione

HRID 2052555Notes

Reaction equation

HRID 2052555 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1)[OH:4].[CH3:15][S:16]([CH3:18])=O.[OH-:19].[K+]>C(=S)=S>[CH3:14][O:13][C:7]1[CH:6]=[C:5]([CH:3]2[O:4][C:15](=[S:16])[NH:1][CH2:2]2)[CH:10]=[CH:9][C:8]=1[O:11][CH3:12].[CH3:14][O:13][C:7]1[CH:6]=[C:5]([CH:3]2[S:16][C:18](=[O:19])[NH:1][CH2:2]2)[CH:10]=[CH:9][C:8]=1[O:11][CH3:12]

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 14797Potassium HydroxideHCID 38639783,4-Dimethoxyphenylethanolamine

Product 2

HCID 203762085-(3,4-Dimethoxyphenyl)-2-oxazolidinethioneYield 9%HCID 203762115-(3,4-Dimethoxyphenyl)-2-thiazolidinoneYield 6%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

45 mmol of 2-amino-1-(3,4-dimethoxyphenyl)-ethanol is dissolved in 65 ml. of absolute dimethyl sulfoxide and combined in succession with 1.8 g. of pulverized potassium hydroxide and 1.4 ml. of carbon disulfide at 10°. The reaction mixture is then stirred under the exclusion of moisture for 2.5 hours. After withdrawing the dimethyl sulfoxide under vacuum, the residue is combined with 100 ml. of water and extracted three times with 100 ml. of chloroform. The combined chloroform phases are dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue is chromatographed over 125 g. of silica gel with chloroform:methanol (96:4). After recrystallization of the corresponding fractions from methanol, a 9% yield of 5-(3,4-dimethoxyphenyl)-2-oxazolidinethione, m.p. 177°-178° is obtained in addition to a 6% yield of 5-(3,4-dimethoxyphenyl)-2-thiazolidinone, m.p. 167°-169°.

Workup

  1. customat 10°
  2. customAfter withdrawing the dimethyl sulfoxide under vacuum
  3. extractionof water and extracted three times with 100 ml
  4. dry with materialThe combined chloroform phases are dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is chromatographed over 125 g
  8. customAfter recrystallization of the corresponding fractions from methanol

Sources & evidence

ORD record
ord-472992eed433454fb16408b61a23da9e
Source dataset
uspto-grants-1980_01
Patent number
US04186129

Reaction notes

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