Chlorosulfonic acid → (+-)-2-But-2-enyl-2-ethylaziridine

HRID 851

Reaction equation

HRID 851 reaction equation
ClS(O)(=O)=O.[NH2:6][C:7]([CH2:14][CH3:15])([CH2:10][CH:11]=[CH:12][CH3:13])[CH2:8]O>C(#N)C>[CH2:10]([C:7]1([CH2:14][CH3:15])[CH2:8][NH:6]1)[CH:11]=[CH:12][CH3:13]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 54018667(+-)-2-Amino-2-ethylhex-4-en-1-ol

Product 1

HCID 54130803(+-)-2-But-2-enyl-2-ethylaziridineYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Chlorosulphonic acid (18 mL) was added to a solution of the product from step (e) (32.3 g) in acetonitrile (100 ml) at least 9° C. When addition was complete, the mixture was warmed to room temperature. The resulting crystals were filtered off, washed with acetonitrile/pet. ether, dried, taken up in a mixture of 50% w/v aqu. KOH (100 mL) and water (55 mL) and distilled over KOH to give the desired product as a colourless oil (16.1 g). 1H NMR consistent with the proposed structure.

Workup

  1. additionWhen addition
  2. filtrationThe resulting crystals were filtered off
  3. washwashed with acetonitrile/pet. ether
  4. customdried
  5. additiontaken up in a mixture of 50%
  6. distillationKOH (100 mL) and water (55 mL) and distilled over KOH

Sources & evidence

ORD record
ord-031db419b85e49eb8266022d09028e45
Source dataset
uspto-grants-1998_03
Patent number
US05723458

Linked notes

Loading…