Triethylamine → HCID 63810511, compound

HRID 2209332Notes

Reaction equation

HRID 2209332 reaction equation
[CH2:1]([C:3]1[NH:4][CH:5]=[CH:6][N:7]=1)[CH3:2].[CH3:8][O:9][CH2:10][CH2:11]Cl.C(N(CC)CC)C>>[CH3:8][O:9][CH2:10][CH2:11][N:4]1[CH:5]=[CH:6][N:7]=[C:3]1[CH2:1][CH3:2]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 123162-Chloroethyl methyl etherHCID 661302-Ethylimidazole

Product 1

HCID 63810511HCID 63810511, compound

Procedure

In an autoclave of 100 mL, 2-ethylimidazole (19.2 g, 200 mmol) was made reacted with chloroethyl methyl ether (22.7 g, 240 mmol) at 140 deg C. for 72 hours. Brown liquid that was obtained was washed with 120 mL of a compound liquid of ethanol and ether (volume ratio thereof is 1:5), and then made reacted with triethylamine (20.2 g, 200 mmol) in the autoclave of 100 mL at 130 deg C. for 24 hours. Solid salts that was formed was removed by filtration, and residue (filtrate) was subjected to reduced-pressure distillation by using a Vigreux column of 20 cm. The product was a transparent liquid which has a boiling point of 160-163 deg C. when a pressure is 10 Pa. 1H-NMR measurement of obtained amine was performed, and it was confirmed that chemical shifts, δ (ppm), are 6.95 (d, 1H), 6.75(d, 1H), 4.08-4.05(t, 2H), 3.62-3.60 (t, 2H), 3.27(s, 3H), 2.68-2.62 (m, 2H), and 1.25-1.22 (t, 3H), and 1-(2-methoxyethyl)-2-ethyl imidazole was synthesized.

Workup

  1. customBrown liquid that was obtained
  2. washwas washed with 120 mL of a compound liquid of ethanol and ether (volume ratio
  3. waitfor 24 hours
  4. customSolid salts that was formed
  5. customwas removed by filtration, and residue (filtrate)
  6. distillationwas subjected to reduced-pressure distillation

Sources & evidence

ORD record
ord-3d34cf28b6be48908ba22c536f8caef5
Source dataset
uspto-grants-2016_06
Patent number
US09379413B2

Reaction notes

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