2-Ethyl-1-butene → HCID 58432618, compound

HRID 1023826Notes

Reaction equation

HRID 1023826 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11]Cl)(=[O:10])=[O:9])=[CH:6][CH:7]=1.[CH2:13]([C:15]([CH2:17][CH3:18])=[CH2:16])[CH3:14].[Br-].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>C(#N)C>[CH2:13]([C:15]1([CH2:17][CH3:18])[CH2:16][N:11]1[S:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)(=[O:10])=[O:9])[CH3:14]

Participants

5

Reactant 3

HCID 129702-Ethyl-1-buteneHCID 31388TosylchloramideHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 58432618HCID 58432618, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Chloramine-T (10 g, 43.9 mmol) was suspended in acetonitrile (146 mL) at room temperature under nitrogen. To this suspension was added 2-ethylbut-1-ene (5.55 g, 65.9 mmol) followed by phenyltrimethylammonium tribromide (1.65 g, 4.39 mmol) in two roughly equal portions. After three days the reaction mixture was concentrated to half volume and then filtered through a sintered glass funnel. The filtrate was concentrated to half volume again which caused further precipitation. This mixture was filtered and the filtrate was partitioned between ethyl acetate and water. The organic phase was dried with MgSO4, filtered and concentrated. The crude material was purified by column chromatography using a Biotage 65i column eluting with (0-100% EtOAc/hexane) to give 2,2-diethyl-1-[(4-methylphenyl)sulfonyl]-aziridine as a colorless solid (4.5 g).

Workup

  1. concentrationAfter three days the reaction mixture was concentrated to half volume
  2. filtrationfiltered through a sintered glass funnel
  3. concentrationThe filtrate was concentrated to half volume again which
  4. customprecipitation
  5. filtrationThis mixture was filtered
  6. customthe filtrate was partitioned between ethyl acetate and water
  7. dry with materialThe organic phase was dried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude material was purified by column chromatography
  11. washeluting with (0-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-07717471ce1d41f5b88ef05d5fd2f854
Source dataset
uspto-grants-2014_05
Patent number
US08722727B2

Reaction notes

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