Acetonitrile → HCID 7230647, compound

HRID 566433Notes

Reaction equation

HRID 566433 reaction equation
[NH2:1][CH:2]([C:8]#[N:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:10]([NH2:14])[CH2:11][CH2:12][CH3:13].[C:15](#N)C>>[NH2:9][C:8]1[N:14]([CH2:10][CH2:11][CH2:12][CH3:13])[CH:15]=[N:1][C:2]=1[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 3

HCID 6342Acetonitrile2×HCID 8007ButylamineHCID 288716Ethyl 2-amino-2-cyanoacetate

Product 1

HCID 7230647HCID 7230647, compoundYield 40%

Procedure

A solution of ethyl 2-amino-2-cyanoacetate (0.20 g, 1.56 mmol) and triethyl formate (0.30 mL, 1.72 mmol) in acetonitrile (5 mL) was refluxed for 1 h. After concentrating the residue was dissolved in a solution of acetonitrile (5 mL) and n-butylamine (0.17 mL, 1.72 mmol). The resulting mixture was stirred at reflux for 1 h. The solvents were removed under reduced pressure and the residue was partitioned between water and ethyl acetate. The organic layer was separated and washed with brine and dried (Na2SO4). After removing the solvent under reduced pressure, flash chromatography (1:1 ethyl acetate/hexane) of the residue gave 0.12 g, 40% of the title compound as an oil: 1H NMR (250 MHz, CDCl3) δ 6.97 (s, 1H), 5.10 (s, 2H), 4.31 (q, 2H), 3.75 (t, 2H), 1.65 (m, 2H), 1.35 (m, 5H), 0.97 (t, 3H); MS(ESI) m/e 212.2 [M+H]+.

Workup

  1. concentrationAfter concentrating the residue
  2. temperatureat reflux for 1 h
  3. customThe solvents were removed under reduced pressure
  4. customthe residue was partitioned between water and ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. customAfter removing the solvent under reduced pressure, flash chromatography (1:1 ethyl acetate/hexane) of the residue

Sources & evidence

ORD record
ord-fa7fc04036cf4d59bbdc9714e24f2450
Source dataset
uspto-grants-2001_01
Patent number
US06174906B1

Reaction notes

Loading…