Acetone → HCID 18323177, compound

HRID 1699115Notes

Reaction equation

HRID 1699115 reaction equation
[CH3:1][S:2][C:3]1[NH:4][C:5](=[O:15])[C:6]([CH3:14])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.CC(C)=O.CC(C)([O-])C.[K+].[C:26]1([S:32]Cl)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1.O>[C:8]1([C:6]2([CH3:14])[C:5](=[O:15])[N:4]([S:32][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:3]([S:2][CH3:1])=[N:7]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 11008040Benzenesulfenyl chlorideHCID 183231654‐Methyl‐2‐(methylsulfanyl)‐4‐phenyl‐4,5‐dihydro‐ 1H‐imidazol‐5‐oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 18323177HCID 18323177, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.6 g (2.7 mmol) of 2-methylthio-4-methyl-4-phenyl-2-imidazolin-5-one in solution in 50 ml of anhydrous tetrahydrofuran (THF) is charged to a 100 ml, three-necked, round-bottomed flask under an inert atmosphere. The solution is stirred with a magnetic stirrer and is cooled to 0° C. (ice bath+acetone). 0.30 g (1 molar equivalent) of potassium tert-butoxide is added and the mixture is stirred for 10 minutes at 0° C. A solution containing 0.40 g of phenylsulfenyl chloride (phenylthio chloride) and 10 ml of anhydrous THF is then run in. The mixture is then left to return to room temperature for one hour. The reaction mixture is run into 100 ml of water. Extraction is carried out with 100 ml of ethyl acetate. The organic phase is washed 4 times with water and dried over sodium sulfate.

Workup

  1. stirringthe mixture is stirred for 10 minutes at 0° C
  2. waitThe mixture is then left
  3. extractionExtraction
  4. washThe organic phase is washed 4 times with water
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-5f01c3f2123448a099480f16a8a62fca
Source dataset
uspto-grants-2002_02
Patent number
US06344564B1

Reaction notes

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