Acetic Acid → (5S)-3-Anilino-5-methyl-5-phenyl-2-sulfanylideneimidazolidin-4-one

HRID 266265Notes

Reaction equation

HRID 266265 reaction equation
[N:1]([C@:4]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:9])[C:5]([O:7]C)=O)=[C:2]=[S:3].[C:16]1([NH:22][NH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C>O>[CH3:9][C@@:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:1][C:2](=[S:3])[N:23]([NH:22][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]1=[O:7]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7516PhenylhydrazineHCID 57098026HCID 57098026, compound

Product 1

HCID 22875031(5S)-3-Anilino-5-methyl-5-phenyl-2-sulfanylideneimidazolidin-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.7 g (0.00316 mol) of methyl (+)-(2S)-2-isothiocyanato-2-phenylpropionate, diluted in 15 ml of dry tetrohydrofuran, is introduced into a 100 ml three-necked flask under a dry nitrogen atmosphere. 0.32 ml (0.00316 mol) of phenylhydrazine, diluted in 5 ml of tetrohydrofuran, is run in at 20° C. in a single step. The temperature rises by 2° C. The medium is kept magnetically stirring for 30 minutes. A dark-beige precipitate appears. The medium is neutralized with 0.4 ml of acetic acid and then treated with 20 ml of water. After separating, the aqueous phase is extracted with 3 times 20 ml of ethyl ether. The organic phases are combined, washed with 2 times 30 ml of water, dried over magnesium sulfate and then concentrated under reduced pressure. The solid residue obtained is chromatographed on a silica column, using an eluent mixture composed of heptane and ethyl acetate in the proportions of 50/50.

Workup

  1. additionis introduced into a 100 ml three-necked flask under a dry nitrogen atmosphere
  2. customis run in at 20° C. in a single step
  3. customrises by 2° C
  4. customAfter separating
  5. extractionthe aqueous phase is extracted with 3 times 20 ml of ethyl ether
  6. washwashed with 2 times 30 ml of water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe solid residue obtained
  10. customis chromatographed on a silica column

Sources & evidence

ORD record
ord-6d28da04f2c644da829297130ef74a78
Source dataset
uspto-grants-1997_07
Patent number
US05650519

Reaction notes

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