Iodoethane → HCID 18323172, compound

HRID 611805Notes

Reaction equation

HRID 611805 reaction equation
[CH3:1][C:2](C)([O-])C.[K+].[CH3:7][S:8][C:9]1[N:10]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11](=[O:20])[CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:13]=1.C(I)C>O1CCCC1.C(OCC)(=O)C>[CH2:1]([C:12]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:11](=[O:20])[N:10]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:9]([S:8][CH3:7])=[N:13]1)[CH3:2]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 18323163HCID 18323163, compound2×HCID 23665647Potassium tert-butoxide

Product 1

HCID 18323172HCID 18323172, compoundYield 40.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.55 g of potassium tert-butoxide is added to a solution of 1.5 g (5.05 mmol) of 2-methylthio-4-phenyl-1-phenylamino-2-imidazolin-5-one (Compound 5) in 50 ml of anhydrous tetrahydrofuran. The mixture is left to react for 30 minutes at room temperature and then 0.8 g (5.05 mmol) of ethyl iodide is added. The mixture is left to react for 1 hour at room temperature. The mixture is diluted with 150 ml of ethyl acetate. The solution is washed with water and then concentrated under reduced pressure. The product is purified by chromatography on a silica column (Merck 60H silica; eluent: 25% ethyl acetate/75% heptane). 0.65 g of Compound 48 is obtained in the form of a beige powder melting at 147° C.

Workup

  1. waitThe mixture is left
  2. customto react for 30 minutes at room temperature
  3. waitThe mixture is left
  4. customto react for 1 hour at room temperature
  5. washThe solution is washed with water
  6. concentrationconcentrated under reduced pressure
  7. customThe product is purified by chromatography on a silica column (Merck 60H silica; eluent: 25% ethyl acetate/75% heptane)

Sources & evidence

ORD record
ord-75655f103a38446fb720ce5eb07db8ec
Source dataset
uspto-grants-1999_12
Patent number
US06002016

Reaction notes

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