Water → HCID 18323184, compound

HRID 1683361Notes

Reaction equation

HRID 1683361 reaction equation
[CH3:1]C(C)([O-])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.CI.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]([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 6328Methyl iodideHCID 15219215HCID 15219215, compound2×HCID 23665647Potassium tert-butoxide

Product 1

HCID 18323184HCID 18323184, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5 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. 0.5 g (3.5 mmol) of methyl iodide is then added and then 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 dried over magnesium sulfate and then concentrated. The product crystallizes when triturated in 10 ml of diisopropyl ether. It is filtered and then dried under vacuum. 0.73 g (yield: 70%) of Compound 22 is thus obtained in the form of a pale-yellow powder melting at 124° 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. dry with materialThe ethereal solution is dried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe product crystallizes when
  9. customtriturated in 10 ml of diisopropyl ether
  10. filtrationIt is filtered
  11. customdried under vacuum

Sources & evidence

ORD record
ord-3df16f068a9f4f5897f6d65cffac151d
Source dataset
uspto-grants-1997_06
Patent number
US05637729

Reaction notes

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