Dimethylformamide dimethyl acetal → Ethyl 3-(dimethylamino)-2-isocyanoacrylate

HRID 990880Notes

Reaction equation

HRID 990880 reaction equation
[N+:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[C-:2].CO[CH:11](OC)[N:12]([CH3:14])[CH3:13]>C(O)C>[CH2:7]([O:6][C:4](=[O:5])[C:3]([N+:1]#[C-:2])=[CH:11][N:12]([CH3:14])[CH3:13])[CH3:8]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 533707Ethyl isocyanoacetate

Product 1

HCID 54355309Ethyl 3-(dimethylamino)-2-isocyanoacrylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl isocyanoacetate (5.0 g) in ethanol (100 mL) is added N,N-dimethyl-formamide dimethyl acetal (6.5 g) dropwise with stirring over 10 minutes. The reaction is stirred for 24 hours and the ethanol is evaporated. The resulting oil is passed through magnesium silicate using 50% ethyl acetate-hexanes as the eluant. The solvents are removed and the resulting oil is crystallized from ethyl acetate-hexanes to yield light yellow needles, 3.0 g.

Workup

  1. stirringThe reaction is stirred for 24 hours
  2. customthe ethanol is evaporated
  3. customThe solvents are removed
  4. customthe resulting oil is crystallized from ethyl acetate-hexanes
  5. customto yield light yellow needles, 3.0 g

Sources & evidence

ORD record
ord-d01f441579fd43c1a4e722e8867a57de
Source dataset
uspto-grants-2002_10
Patent number
US06462055B2

Reaction notes

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