Thiophosgene → Ethyl 2-isothiocyanato-4,5-dimethylthiophene-3-carboxylate

HRID 44380

Reaktionsgleichung

Reaktionsgleichung von HRID 44380
[C:1](Cl)(Cl)=[S:2].C(=O)([O-])[O-].[Ca+2].[NH2:10][C:11]1[S:12][C:13]([CH3:22])=[C:14]([CH3:21])[C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(Cl)(Cl)Cl.O.C(Cl)(Cl)Cl>[N:10]([C:11]1[S:12][C:13]([CH3:22])=[C:14]([CH3:21])[C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:1]=[S:2]

Komponenten

6

Edukt 3

HCID 10040ThiophosgeneHCID 10112Calcium CarbonateHCID 78536Ethyl 2-amino-4,5-dimethyl3-thenoate

Produkt 1

HCID 3419522Ethyl 2-isothiocyanato-4,5-dimethylthiophene-3-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 22418719Chloroform waterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of thiophosgene (5.10 mL, 7.64 mmol) and calcium carbonate (1.05 g, 10.54 mmol) in CHCl3/H2O (½ by volume, 6 mL) was added dropwise a solution of ethyl 2-amino-4,5-dimethylthiophene-3-carboxylate (1.05 g, 5.27 mmol) in CHCl3 (7 mL) at 0° C. over a period of 1 h. The reaction mixture was the stirred for 2.5 h at 0° C., washed with water (3×). The organic layer was dried over MgSO4, filtered and concentrated to give the title compound (1.21 g, 100%). 1H NMR (400 MHz, DMSO-d6) δ1.32 (t, 3H, J=7.1 Hz), 2.19 (s, 3H), 2.30 (s, 3H), 4.28 (q, 2H, J=7.1 Hz).

Aufarbeitung

  1. washwashed with water (3×)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4e8d5b38f8ff45c4b7c87165d7d2657d
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541421B2

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