Cyanamide → N,N′-Dicyanocyclopropanecarboximidamide

HRID 868296Notes

Reaction equation

HRID 868296 reaction equation
[N:1]#[C:2][NH2:3].C[O-].[Na+].CO[C:9]([CH:13]1[CH2:15][CH2:14]1)=[N:10][C:11]#[N:12]>CO>[C:2]([NH:3][C:9]([CH:13]1[CH2:15][CH2:14]1)=[N:10][C:11]#[N:12])#[N:1]

Participants

5

Conditions

Temperature
10 °C

Procedure

At 0° C. 8,4 g of cyanamide in 50 ml methanole are added to 36 g of a 30% solution of sodium methylate in methanol and stirred for 30 min. at 10° C. The resulting solution is then cooled to -20° C. and mixed with a solution of 22 g N-cyano-cyclopropanecarboximidic acid methylester in 60 ml methanole. The reaction mixture is then stirred for 30 min. at 20° C. and then evaporated. 100 ml of dioxane is added to the resulting residue which is then concentrated by evaporation. Then again 100 ml of toluene is added and the solution is concentrated at an ambient temperature of 60° C. up to a residual weight of 33 g.

Workup

  1. customAt 0° C
  2. temperatureThe resulting solution is then cooled to -20° C.
  3. stirringThe reaction mixture is then stirred for 30 min. at 20° C.
  4. customevaporated
  5. addition100 ml of dioxane is added to the resulting residue which
  6. concentrationis then concentrated by evaporation
  7. additionThen again 100 ml of toluene is added
  8. concentrationthe solution is concentrated at an ambient temperature of 60° C. up to a residual weight of 33 g

Sources & evidence

ORD record
ord-7b8a917ec6bf481e9a45ad2380895c73
Source dataset
uspto-grants-1988_10
Patent number
US04778889

Reaction notes

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