Show

 Reaction Published on 2022-02-20 This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License. 


Contributor: Joshua Heck

1. Institute of Inorganic Chemistry, Rheinisch Westfälische Technische Hochschule Aachen, Germany

Authors: Joshua Heck1 - Sonja Herres-Pawlis2 - Alexander Hoffmann3

1. Institute of Inorganic Chemistry, Rheinisch Westfälische Technische Hochschule Aachen, Germany

2. Fachgruppe Chemie, Rheinisch Westfälische Technische Hochschule Aachen, Germany

3. Rheinisch Westfälische Technische Hochschule Aachen, Germany

Reaction DOI: 
Reaction ID: 
Reference in the Literature:

Reaction Table  
IUPACFormulaDensity/MolarityAmount [mg]Volume [mL]Amount [mmol]Equiv
Starting materials
2-tert-butylquinolin-8-amineC13H16N2- / -3900.000 - 19.4731.000
Reactants
N,N,N',N'-TetramethylchlorformamidiniumchloridC5H12Cl2N2- / -3997.408 - 23.3671.200
N,N-diethylethanamineC6H15N- / -3940.902 - 38.9462.000
Products
2-(2-tert-butylquinolin-8-yl)-1,1,3,3-tetramethylguanidineC18H26N4- / -4400.000 - 14.74476%
Solvents
AcetonitrileC2H3N - 60.000 - 100%
Description:

2-tert-Butyl-8-aminoquinoline (3.90 g, 19.5 mmol, 1 eg.) and TMG-VS (4.00 g, 23.4 mmol, 1.2 eq.) were dissolved in MeCN (60 mL) and triethylamine (5.4 mL, 38.9 mmol, 2 eq.) was added. The reaction mixture was heated to reflux for 30 min under stirring. After cooling to rt a solution of NaOH (0.78 g, 19.5 mmol, 1 eq.) in water (2 ml) was added and the solvent was removed under reduced pressure. An aqueous KOH solution (25 mL, 50 w%) was added and the aqueous layer was extracted with MeCN (3x 100 mL). The combined organic layers were dried over Na2SO4 and filtered. The solvent was removed under reduced pressure and the crude product was distillated in vacuum (<10-1 mbar) starting at 150 °C and increasing the temperature stepwise up to 350 °C. Remained urea was removed in vacuum (<10-1 mbar) at 100 °C. TMG2tBuqu was obtained as a pale yellow solid (4.40 g, 14.74 mmol, 76%).

RInChiKey Table  
Properties  
Status: Successful
Temperature: 95 °C
Duration: 30 Minute(s)
TLC-Control  
Solvents (parts)
Rf-Value
0
TLC-Description
Analyses  
1H NMR, 13C NMR, ATR-FTIR, HR-ESI-TOF-MS

 Product  

IUPAC Name: 2-(2-tert-butylquinolin-8-yl)-1,1,3,3-tetramethylguanidine (C18H26N4)
Canonical SMILES:
CN(C(=Nc1cccc2c1nc(cc2)C(C)(C)C)N(C)C)C
InChI:
InChI=1S/C18H26N4/c1-18(2,3)15-12-11-13-9-8-10-14(16(13)20-15)19-17(21(4)5)22(6)7/h8-12H,1-7H3
InChIKey:
DYIBODSCVMVCNX-UHFFFAOYSA-N
Exact Mass: 298.215747 g⋅mol-1
Sample DOI:
Sample ID:
Reference in the Literature:

    1H nuclear magnetic resonance spectroscopy (1H NMR)  
    Analysis DOI:
    Analysis ID:

    1H NMR (400 MHz, Chloroform-d [7.27 ppm], ppm) δ = 7.97 (d, J = 8.7 Hz, 1H), 7.40 (d, J = 8.6 Hz, 1H), 7.35 (t, J = 7.9 Hz, 1H), 7.23–7.20 (m, 2H), 2.67 (s, 12H), 1.38 (s, 9H).

    13C nuclear magnetic resonance spectroscopy (13C NMR)  
    Analysis DOI:
    Analysis ID:

    13C NMR (100 MHz, Chloroform-d [77.0 ppm], ppm) δ = 166.5, 162.2, 150.4, 141.1, 136.2, 127.4, 126.6, 120.7, 118.3, 117.9, 39.7 (4C), 38.4, 30.2 (3C).

    attenuated total reflectance Fourier transform infrared spectroscopy (ATR-FTIR)  
    Analysis DOI:
    Analysis ID:

    IR (ATR, ṽ) = 2989 (w), 2946 (m), 2920 (m), 2887 (m), 2864 (m), 2793 (w), 1608 (vs), 1597 (vs), 1556 (s), 1495 (vs), 1474 (w), 1452 (m), 1444 (s), 1430 (s), 1420 (m), 1388 (w), 1370 (vs), 1363 (vs), 1342 (m), 1307 (m), 1271 (w), 1230 (s), 1214 (m), 1178 (w), 1134 (vs), 1125 (vs), 1105 (w), 1081 (m), 1056 (s), 1008 (vs), 924 (w), 900 (m), 872 (w), 843 (vs), 822 (w), 811 (w), 778 (vs), 770 (m), 752 (m), 719 (m), 679 (s), 645 (w), 628 (w), 564 (m), 540 (w), 502 (w), 457 (m), 427 (w) cm–1.

    Datasets
    high-resolution electrospray ionisation time-of-flight mass spectrometry (HR-ESI-TOF-MS)  
    Analysis DOI:
    Analysis ID:

    HRMS (ESI+, MeOH): m/z (found) = 299.22232 (100 %), 300.22559 (20 %), 301.22864 (2 %); m/z (calc.) = 299.22302 (100 %, 12C181H2714N4+), 300.22638 (20 %, 12C1713C1H2714N4+), 301.22973 (2 %, 12C1613C21H2714N4+).