Iodoethane → HCID 18323172, compound

HRID 266259Notes

Reaction equation

HRID 266259 reaction equation
[K].[O-][CH2:3][CH2:4]CC.[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>[CH2:3]([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)[CH3:4]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 5462222PotassiumHCID 12476378Butan-1-olateHCID 18323163HCID 18323163, compound2×

Product 1

HCID 18323172HCID 18323172, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.55 g of potassium ten-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 more 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 more 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-092204c277a84700851cae30e63fb7e9
Source dataset
uspto-grants-1997_07
Patent number
US05650519

Reaction notes

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