Water → HCID 18323168, compound

HRID 266258Notes

Reaction equation

HRID 266258 reaction equation
[CH3:1][C:2](C)([O-:4])C.[K+].[CH3:7][C:8]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:12](=[O:13])[N:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]([S:21][CH3:22])=[N:9]1.C(Cl)(=O)C.O>O1CCCC1>[CH3:7][C:8]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:12](=[O:13])[N:11]([N:14]([C:2](=[O:4])[CH3:1])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]([S:21][CH3:22])=[N:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 15219215HCID 15219215, compound2×HCID 23665647Potassium tert-butoxide

Product 1

HCID 18323168HCID 18323168, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

0.4 g (3.5 mmol) of potassium tert-butoxide is added to a solution of 4-methyl-1-phenylamino-2-methylthio-4-phenyl-2-imidazolin-5-one (Compound 9) (1 g, 3.2 mmol) in anhydrous tetrahydrofuran (30 ml), cooled beforehand to 0° C. The mixture is left to react for 0.5 hour at 0° C. 0.25 g (3.5 mmol) of acetyl chloride is then added and the mixture is left to react for 0.5 hour at room temperature. The reaction mixture is poured into 100 ml of water and the product is extracted with 100 ml of diethyl ether. The ethereal solution is washed with water to neutrality. The solution is dried over magnesium sulfate and then concentrated. A honey-like product is obtained which is purified by chromatography on a silica column. The purified product crystallizes from diisopropyl ether. 0.25 g of Compound 23 is obtained in the form of a white powder melting at 132° C.

Workup

  1. waitThe mixture is left
  2. customto react for 0.5 hour at 0° C
  3. waitthe mixture is left
  4. customto react for 0.5 hour at room temperature
  5. extractionthe product is extracted with 100 ml of diethyl ether
  6. washThe ethereal solution is washed with water to neutrality
  7. dry with materialThe solution is dried over magnesium sulfate
  8. concentrationconcentrated
  9. customA honey-like product is obtained which
  10. customis purified by chromatography on a silica column
  11. customThe purified product crystallizes from diisopropyl ether

Sources & evidence

ORD record
ord-33fe85750f29432bbf912812668ed0c5
Source dataset
uspto-grants-1997_07
Patent number
US05650519

Reaction notes

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