Carbon Dioxide → 2-[(N-Methyl-N-n-octadecylamino)methyl]-2-propenenitrile

HRID 1156370Notes

Reaction equation

HRID 1156370 reaction equation
[C:1]([CH2:3][C:4](O)=O)#[N:2].[CH3:7][NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C=O.[C:29](=O)=O>O1CCOCC1>[CH3:7][N:8]([CH2:29][C:3](=[CH2:4])[C:1]#[N:2])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 280Carbon Dioxide2×HCID 712FormaldehydeHCID 9740Cyanoacetic acidHCID 75539N-Methyloctadecylamine

Product 1

HCID 128514082-[(N-Methyl-N-n-octadecylamino)methyl]-2-propenenitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of cyanacetic acid (2.6 g., 0.03 mole) and N-methyl-N-octadecylamine (8.4 g., 0.03 mole) in 25 ml. of dioxane at room temperature is added 38% aqueous formaldehyde (5.4 g., 0.06 mole) dropwise over about 2 minutes. The resultant mixture is then heated gently in a hot water bath until a clear solution is obtained and carbon dioxide is released vigorously (ca. 60° C. bath). When the evolution of carbon dioxide is complete, the mixture is allowed to cool, and the volatiles removed in vacuo to yield 9.2 g. of the substituted propenenitrile as an off-white solid.

Workup

  1. customis obtained
  2. custom(ca. 60° C. bath)
  3. temperatureto cool
  4. customthe volatiles removed in vacuo
  5. customto yield 9.2 g

Sources & evidence

ORD record
ord-d00b61cf00da495c83fc4c565d3644ca
Source dataset
uspto-grants-1982_06
Patent number
US04335141

Reaction notes

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