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

HRID 649298Notes

Reaction equation

HRID 649298 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:1]([NH:3][C:4]([N:14]1[CH2:16][CH2:15]1)=[N:12][CH3:13])#[N:2]

Participants

3

Reactant 2

HCID 9033AziridineHCID 13186920HCID 13186920, compound

Product 1

HCID 13150956N-cyano-N'-methyl-1-aziridinoamidineYield 57.7%

Procedure

N-Cyano-N'-methyl-O-phenylisourea (10.0 g, 0.0571 mol) was added in half-gram batches during 6 min to aziridine (7.926 g, 0.184 mol) cooled to 0° and stirred. A solution was formed, from which after 5 min a colourless solid crystallised out. The reaction mixture was stirred at 20° for 90 min. and then cooled to 0° to complete crystallisation. Filtration and washing the residue with cold ether gave crystalline N-cyano-N'-methyl-1-aziridinoamidine (4.09 g, 57%), m.p. 134°-135°, Rf 0.64-0.66 (silica, acetonitrile). Further product (1.78 g) was isolated from the ether washings, giving a total yield of 5.87 g, 82%.

Workup

  1. temperaturecooled to 0°
  2. customA solution was formed, from which after 5 min a colourless solid
  3. customcrystallised out
  4. stirringThe reaction mixture was stirred at 20° for 90 min.
  5. temperaturecooled to 0°
  6. customcrystallisation
  7. filtrationFiltration
  8. washwashing the residue with cold ether

Sources & evidence

ORD record
ord-08c49353879a4d3ca4ea1603aeb3832b
Source dataset
uspto-grants-1988_04
Patent number
US04739077

Reaction notes

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