Triethylamine → Methyl 2-[(3-Bromopropylimino)methyl]phenylcarbamate

HRID 1520756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1520756
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:13])[O:11][CH3:12])=O.S([O-])([O-])(=O)=O.[Mg+2].Cl.[Br:21][CH2:22][CH2:23][CH2:24][NH2:25].C(N(CC)CC)C>C(Cl)(Cl)Cl>[Br:21][CH2:22][CH2:23][CH2:24][N:25]=[CH:1][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:13])[O:11][CH3:12]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 128607653-Bromopropan-1-amine--hydrogen chloride (1/1)HCID 45122974Methyl (2-formylphenyl)carbamate

Produkt 1

HCID 49856372Methyl 2-[(3-Bromopropylimino)methyl]phenylcarbamateAusbeute 94,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Methyl 2-formylphenylcarbamate (7, 2.5 g, 14 mmol) and magnesium sulfate (5 g) were added to a solution of 3-bromopropylamine hydrochloride (3.68 g, 16.8 mmol) and triethylamine in chloroform (30 mL) and mixture was stirred for 24 h. The mixture was filtered and the residue was washed with chloroform (2×30 mL). The combined filtrates were washed with water (2×30 mL), brine (30 mL), dried with sodium sulfate, and concentrated to afford 21 as a yellow oil (3.95 g, 94.5%). IR (film) 1730, 1638 cm−1; 1H NMR (300 MHz, CDCl3) δ 8.38 (d, J=8.4 Hz, 1 H), 8.30 (s, 1 H), 7.35 (t, J=7.7 Hz, 2 H), 7.26 (d, J=7.7 Hz, 1 H), 7.00 (t, J=7.4 Hz, 1 H), 3.74 (s, 3 H), 3.69 (t, J=6.3 Hz, 2 H), 3.50 (t, J=6.6 Hz, 2 H), 2.20 (pent, J=6.3 Hz, 2 H); 13C NMR (75 MHz, CDCl3) δ 164.74, 154.30, 140.07, 133.00, 131.32, 121.25, 119.79, 117.69, 58.17, 52.87, 33.16, 31.15; ESIMS m/z (rel intensity) 299/301 (MH+, 100/99); EIHRMS m/z M+ calcd. for C12H15BrN2O2, 298.0317; found, 298.0320.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. washthe residue was washed with chloroform (2×30 mL)
  3. washThe combined filtrates were washed with water (2×30 mL), brine (30 mL)
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0d28dd345df04f348f6c09dd33835276
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073920B2

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