Diethylamine → HCID 12179642, compound

HRID 1919317Notes

Reaction equation

HRID 1919317 reaction equation
[N+:1]([CH2:3][C:4]([O:6]C)=O)#[C-:2].[CH2:8]([NH:10][CH2:11][CH3:12])[CH3:9]>>[CH2:8]([N:10]([CH2:11][CH3:12])[C:4](=[O:6])[CH2:3][N+:1]#[C-:2])[CH3:9]

Participants

3

Reactant 2

HCID 8021DiethylamineHCID 547815Methyl isocyanoacetate

Product 1

HCID 12179642HCID 12179642, compoundYield 25,034.9%

Procedure

To stirred and cooled (0° C.) methyl 2-isocyanoacetate (96% technical grade, 2.51 g, 25.36 mmol) was slowly added diethylamine (2.78 g, 38.04 mmol). The mixture was stirred for 16 h at 52° C. and then concentrated. The resulting oil was co-evaporated twice with CH2Cl2:hexane, and purified using column chromatography (SiO2, eluent cyclohexane:EtOAc=6:4) to yield after evaporation and drying N3N-diethyl-2-isocyanoacetamide, SLA 19136, as a brown oil (890 g, 25% yield).

Workup

  1. stirringThe mixture was stirred for 16 h at 52° C.
  2. concentrationconcentrated
  3. customhexane, and purified
  4. customto yield
  5. customafter evaporation
  6. dry with materialdrying N3N-diethyl-2-isocyanoacetamide, SLA 19136

Sources & evidence

ORD record
ord-d34306216de9438ebcadd4a367e604a9
Source dataset
uspto-grants-2012_05
Patent number
US08168631B2

Reaction notes

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