Triethylamine → HCID 22258323, Verbindung

HRID 1610917Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1610917
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][O:13][CH3:14])[CH2:6][NH2:7].[C:15](Cl)(Cl)=[S:16].C(N(CC)CC)C>C(OCC)(=O)C>[N:7]([CH2:6][C:5]1[CH:8]=[CH:9][C:10]([O:11][CH2:12][O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=1)=[C:15]=[S:16]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 222583273-Methoxy-4-methoxymethoxybenzylamine

Produkt 1

HCID 22258323HCID 22258323, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

A solution of 3-methoxy-4-methoxymethoxybenzylamine (5.3 g, 26.9 mmol) in ethyl acetate (50 mL) was added, via an addition funnel) to a solution of thiophosgene (2.15 mL, 28.2 mmol) and triethylamine (7.87 mL, 56.5 mmol) in ethyl acetate (30 mL) at 0° C. The resultant solution was stirred at ambient temperature overnight. The solution was washed with saturated aqueous sodium bicarbonate and dried over sodium sulfate. The solvent was evaporated in vacuo, and the residue was purified by flash chromatography on silica gel eluted with ethyl acetate/hexanes (1/9 to 3/7) to give the product, 4-isothiocyanatomethyl-2-methoxy-1-methoxymethoxy-benzene, as a waxy tan solid, 4.9 g (76%). 1H NMR (CDCl3): δ 3.51 (s, 3H), 3.91 (s, 3 H), 4.64 (s, 2 H), 5.23 (s, 2 H), 6.83 (m, 2 H) and 7.14 (d, J=8 Hz).

Aufarbeitung

  1. washThe solution was washed with saturated aqueous sodium bicarbonate
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by flash chromatography on silica gel
  5. washeluted with ethyl acetate/hexanes (1/9 to 3/7)

Quellen und Nachweise

ORD-Eintrag
ord-6338e06d351a4c5fac88fc39175bbbdd
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06984647B2

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