Triethylamine → HCID 82651084, compound

HRID 1749428Notes

Reaction equation

HRID 1749428 reaction equation
[CH3:1][N:2]([CH:4]=[C:5]([C:8](=O)[CH2:9][CH3:10])[C:6]#[N:7])C.Cl.C(N)=[NH:14].C(N(CC)CC)C>C(O)C>[CH2:9]([C:8]1[C:5]([C:6]#[N:7])=[CH:4][N:2]=[CH:1][N:14]=1)[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 118162249HCID 118162249, compound

Product 1

HCID 82651084HCID 82651084, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of crude 2-((dimethylamino)methylene)-3-oxopentanenitrile (0.98 equiv.), formamidine hydrochloride (2.0 equiv.) and triethyl amine (2.0 equiv.) in ethanol (1.0 M) was refluxed for 36 h. The solvent was removed and the residue was purified by silica column chromatography (20% ethyl acetate in petroleum ether) to afford the title product (35% yield). 1H-NMR (400 MHz, CDCl3) δ (ppm) 9.20 (s, 1H), 8.83 (s 1H), 2.98 (d, J=7.6 Hz, 2H), 1.32 (t, J=7.6 Hz, 3H); MS (ESI) m/z 134.1 [M+H]+.

Workup

  1. temperaturewas refluxed for 36 h
  2. customThe solvent was removed
  3. customthe residue was purified by silica column chromatography (20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-917ee1f4450e467a996b0e9e42e87e0d
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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