Chlorosulfonic acid → (R)-2-Butyl-2-ethylaziridine

HRID 342869Notes

Reaction equation

HRID 342869 reaction equation
ClS(O)(=O)=O.[CH2:6]([C:10]1([CH2:13][CH3:14])[CH2:12][NH:11]1)[CH2:7][CH2:8][CH3:9]>ClC(Cl)C>[CH2:6]([C@:10]1([CH2:13][CH3:14])[CH2:12][NH:11]1)[CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 217099702-Butyl-2-ethylaziridine

Product 1

HCID 53812986(R)-2-Butyl-2-ethylaziridineYield 77%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Chlorosulphonic acid (1 molar equivalent) was added to a solution of the product from step (f) (15 g) in dichloroethane (90 ml) at a temperature of <16° C. When addition was complete, the mixture was stirred for 2 hours at room temperature and then evaporated in vacuo. Water (60 ml) and 5% w/v aqu. NaOH (41 ml) were added and the mixture distilled at atmospheric pressure. The organic phase of the distillate was separated and dried over KOH to give a solution of the desired product (77% yield).

Workup

  1. additionWhen addition
  2. customevaporated in vacuo
  3. additionNaOH (41 ml) were added
  4. distillationthe mixture distilled at atmospheric pressure
  5. customThe organic phase of the distillate was separated
  6. dry with materialdried over KOH

Sources & evidence

ORD record
ord-bcd591f56ef74c39a95b82a1fd46c7ab
Source dataset
uspto-grants-1999_01
Patent number
US05859240

Reaction notes

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