Diallylamine → 3-(Cyanoimino)-3-(N,N-diallylamino)propionitrile

HRID 437858Notes

Reaction equation

HRID 437858 reaction equation
[C:1]([N:3]=[C:4](OCC)[CH2:5][C:6]#[N:7])#[N:2].[CH2:11]([NH:14][CH2:15][CH:16]=[CH2:17])[CH:12]=[CH2:13]>O1CCCC1>[C:1]([N:3]=[C:4]([N:14]([CH2:15][CH:16]=[CH2:17])[CH2:11][CH:12]=[CH2:13])[CH2:5][C:6]#[N:7])#[N:2]

Participants

4

Reactant 2

HCID 31279DiallylamineHCID 12272864Ethanimidic acid, N,2-dicyano-, ethyl ester

Product 1

HCID 214271633-(Cyanoimino)-3-(N,N-diallylamino)propionitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.00 g (0.0292 m) ethyl N,2-dicyanoacetimidate and 2.83 g (0.0292 m) diallylamine in 60 ml tetrahydrofuran is stirred at 0° C. for twelve hours. The reaction is concentrated and filtered through silica gel (2% MeOH/CH2Cl2 eluent). The organic phase is concentrated and the residue chromatographed (HPLC, 1"× 40" of 30-50 μ silica gel, 2% MeOH/CH2Cl2) to give product. A minor impurity (200 mg) crystallizes out from CH2Cl2 -C6H12. The residual oil (3.08 g, 56%) has nmr, ir, and mass spec which are consistent.

Workup

  1. concentrationThe reaction is concentrated
  2. filtrationfiltered through silica gel (2% MeOH/CH2Cl2 eluent)
  3. concentrationThe organic phase is concentrated
  4. customthe residue chromatographed (HPLC, 1"× 40" of 30-50 μ silica gel, 2% MeOH/CH2Cl2)
  5. customto give product
  6. customA minor impurity (200 mg) crystallizes out from CH2Cl2 -C6H12

Sources & evidence

ORD record
ord-679188f2f1da40838d32cc61efa485cd
Source dataset
uspto-grants-1977_06
Patent number
US04032559

Reaction notes

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