Triethylamine → Imidazole-1-carboxylic acid hex-5-enyl methyl amide

HRID 880730Notes

Reaction equation

HRID 880730 reaction equation
S([C:5]1[CH:11]=[CH:10][C:8](C)=[CH:7][CH:6]=1)(O)(=O)=O.CNCCCCC=C.[C:20]([N:27]1C=CN=[CH:28]1)([N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)=[O:21].C(N(CC)CC)C>CN(C=O)C>[CH2:6]([N:27]([CH3:28])[C:20]([N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)=[O:21])[CH2:7][CH2:8][CH2:10][CH:11]=[CH2:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 46737741N-methylhex-5-en-1-amine 4-methylbenzenesulfonate

Product 1

HCID 59533450Imidazole-1-carboxylic acid hex-5-enyl methyl amideYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 2a (3 g, 1 eq.), carbonyldiimidazole (2.04 g, 1.2 eq.), and triethylamine (1.74 g, 1.2 eq.) in anhydrous DMF (60 mL) were stirred at room temperature for 2 days. The reaction mixture was then washed with water. Organics were dried over Na2SO4, filtered, and concentrated under reduced pressure to yield compound 3a as a pale yellow oil in 94% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 1.33 (quint, J=8.04 Hz, 2H), 1.61 (quint, J=8.04 Hz, 2H), 2.02 (q, J=7.46 Hz, 2H), 3.00 (s, 3H), 3.05 (t, J=7.46 Hz, 2H), 3.35 (t, J=7.46 Hz, 1H), 4.89-4.96 (m, 2H), 7.02 (m, 1H), 7.15 (m, 1H), 7.81 (s, 1H).

Workup

  1. washThe reaction mixture was then washed with water
  2. dry with materialOrganics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0b3effb08374eb586515b018b4476cf
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

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