Iodoethane → HCID 19779505, compound

HRID 2082076Notes

Reaction equation

HRID 2082076 reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[CH2:4][CH2:5][CH2:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)(=[NH:9])=[O:8])[CH3:2].[H-].[Na+].I[CH2:24][CH3:25]>CN(C)C=O.O>[CH2:24]([N:9]=[S:7]([CH2:6][CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:19][CH3:20])([C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)=[O:8])[CH3:25]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 9904386HCID 9904386, compound

Product 1

HCID 19779505HCID 19779505, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of S-(3-diethylaminopropyl)-S-(4-nitrophenyl)sulfoximine (10 mmol) in dimethylformamide is added to a stirred suspension of 60% sodium hydride-oil dispersion (10 mmol) at ambient temperature. After stirring for 30 min the mixture is warmed to 50° C. for 30 min and then cooled to ambient temperature. Iodoethane (10 mmol) is added dropwise to the reaction mixture and stirred at ambient temperature for 30 min and then warmed to 50° C. for 1 hr. The reaction mixture is diluted with water and extracted with methylene chloride. The methylene chloride extract is concentrated in vacuo and the residue partitioned between methylene chloride-1N hydrochloric acid. The acid layer is separated and basified with 50% sodium hydroxide solution and extracted with methylene chloride. The methylene chloride extract is washed with water, dried, and concentrated to obtain the title compound.

Workup

  1. temperaturecooled to ambient temperature
  2. stirringstirred at ambient temperature for 30 min
  3. temperaturewarmed to 50° C. for 1 hr
  4. extractionextracted with methylene chloride
  5. extractionThe methylene chloride extract
  6. concentrationis concentrated in vacuo
  7. customthe residue partitioned between methylene chloride-1N hydrochloric acid
  8. customThe acid layer is separated
  9. extractionextracted with methylene chloride
  10. extractionThe methylene chloride extract
  11. washis washed with water
  12. customdried
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-ae6fcc5fb4b6492b969e7ec592992166
Source dataset
uspto-grants-1993_02
Patent number
US05187189

Reaction notes

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