Aziridine → N-cyano-N'-methyl-1-aziridinoamidine

HRID 649297Notes

Reaction equation

HRID 649297 reaction equation
[C:1]([NH:3][C:4](=[N:12][CH3:13])OC1C=CC=CC=1)#[N:2].[NH:14]1[CH2:16][CH2:15]1>C(#N)C>[C:1]([NH:3][C:4]([N:14]1[CH2:16][CH2:15]1)=[N:12][CH3:13])#[N:2]

Participants

4

Reactant 2

HCID 9033AziridineHCID 13186920HCID 13186920, compound

Product 1

HCID 13150956N-cyano-N'-methyl-1-aziridinoamidineYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Cyano-N'-methyl-O-phenylisourea (0.471 g, 2.69 mmol) was added during 2 minutes to aziridine (0.521 g, 12.1 mmol) at 20° with stirring. Immediate solution occurred, some heat was evolved, and after 5 min a solid precipitate was formed. After 90 min excess aziridine was removed in an air stream at 20°, leaving an oily solid residue. This was dissolved in acetonitrile (10 ml) and the solution was absorbed on to silica gel (1.0 g), and remaining volatiles were removed by evaporation under reduced pressure at 20°. The solid obtained was added to the top of a column of silica gel (19.7 g, length 15 cm, diameter 2 cm) and the column eluted with acetonitrile. The elution of phenol was followed by TLC and after it was complete, subsequent eluate was collected and gave on evaporation to dryness under reduced pressure N-cyano-N'-methyl-1-aziridinoamidine (0.257 g, 77%), m.p. 130°-132.5°, Rf 0.64-0.66 (silica, acetonitrile).

Workup

  1. customafter 5 min a solid precipitate was formed
  2. customAfter 90 min excess aziridine was removed in an air stream at 20°
  3. customleaving an oily solid residue
  4. customthe solution was absorbed on to silica gel (1.0 g)
  5. customwere removed by evaporation under reduced pressure at 20°
  6. customThe solid obtained
  7. additionwas added to the top of a column of silica gel (19.7 g, length 15 cm, diameter 2 cm)
  8. washthe column eluted with acetonitrile
  9. washThe elution of phenol
  10. customsubsequent eluate was collected

Sources & evidence

ORD record
ord-8ec1792ae5fc4df782364e7dc58301be
Source dataset
uspto-grants-1988_04
Patent number
US04739077

Reaction notes

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