Diethyl Ether → HCID 15065506, compound

HRID 846659Notes

Reaction equation

HRID 846659 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].C(O[CH:8](OCC)[CH2:9][NH:10][CH2:11][C:12]#[CH:13])C.[CH3:17]COCC>>[CH3:1][N:2]1[CH:8]=[CH:9][N:10]([CH:11]([CH3:17])[C:12]#[CH:13])[C:3]1=[O:4]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 12228Methyl IsocyanateHCID 15065591HCID 15065591, compound

Product 1

HCID 15065506HCID 15065506, compound

Conditions

Temperature
50 °C

Procedure

Methyl isocyanate (4.6 g, 0.081 mol) was added to a stirred solution of 2,2-diethoxy-N-(2-propynyl)ethylamine (13.7 g, 0.074 mol) in ether (150 mL). After 30 min the ether was evaporated and the residue was dissolved in water (150 mL), oxalic acid (6.7 g) was added, and the solution was heated at 50° C. for 30 min. The solution was then concentrated to 20 mL and neutralized with 4N NaOH solution, and extracted with ethyl acetate (4×150 mL). The ethyl acetate was evaporated and the residue was chromatographed on silica gel to give 9.6 g of product as an oil.

Workup

  1. customAfter 30 min the ether was evaporated
  2. dissolutionthe residue was dissolved in water (150 mL)
  3. additionoxalic acid (6.7 g) was added
  4. concentrationThe solution was then concentrated to 20 mL and neutralized with 4N NaOH solution
  5. extractionextracted with ethyl acetate (4×150 mL)
  6. customThe ethyl acetate was evaporated
  7. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-479bca9d1d59462aa80ee37a1c9c18ff
Source dataset
uspto-grants-1992_08
Patent number
US05137905

Reaction notes

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