Chlorosulfonic acid → 2-Butyl-2-ethylaziridine

HRID 398812Notes

Reaction equation

HRID 398812 reaction equation
[NH2:1][C:2]([CH2:9][CH3:10])([CH2:5][CH2:6][CH2:7][CH3:8])[CH2:3]O.ClS(O)(=O)=O>C(#N)C>[CH2:5]([C:2]1([CH2:9][CH3:10])[CH2:3][NH:1]1)[CH2:6][CH2:7][CH3:8]

Participants

4

Procedure

Acetonitrile (150 ml) and the product from (e) (20.0 g) were mixed under nitrogen, cooled to 2°-3° C. and chlorosulphonic acid (16.0 g, Aldrich) was added dropwise keeping the temperature below 10° C. The coolant was removed and the slurry left to stir for 80 minutes at room temperature. The reaction was concentrated in vacuo and co-distilled with water (50 ml). 50% Aqueous sodium hydroxide (55.2 g) and water (50 ml) were added and the mixture was distilled at atomospheric pressure. The organic layer was collected from the distillate and dried with solid potassium hydroxide to give the desired product (12.8 g). 1H NMR consistent with proposed structure.

Workup

  1. temperaturecooled to 2°-3° C.
  2. customthe temperature below 10° C
  3. customThe coolant was removed
  4. waitthe slurry left
  5. concentrationThe reaction was concentrated in vacuo and co-distilled with water (50 ml)
  6. addition50% Aqueous sodium hydroxide (55.2 g) and water (50 ml) were added
  7. distillationthe mixture was distilled at atomospheric pressure
  8. distillationThe organic layer was collected from the distillate
  9. dry with materialdried with solid potassium hydroxide

Sources & evidence

ORD record
ord-a0d50442749a456d92c9e208b09d463e
Source dataset
uspto-grants-1998_10
Patent number
US05817652

Reaction notes

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