1,2-Dichloroethane → HCID 22250084, Verbindung

HRID 889898Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889898
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[S:12][C:13]([C:17]([OH:19])=O)=[C:14]([CH3:16])[N:15]=3)[S:10][C:3]=12.[Cl:20]CCCl.CN(C)C=O.S(Cl)(Cl)=O>C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[S:12][C:13]([C:17]([Cl:20])=[O:19])=[C:14]([CH3:16])[N:15]=3)[S:10][C:3]=12

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 22250074HCID 22250074, Verbindung

Produkt 1

HCID 22250084HCID 22250084, VerbindungAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 4 g (12.9 mmol) of 2-(7-chloro-thieno[3,2-b]pyridin-2-yl)-4-methyl-thiazole-5-carboxylic acid 40 mL of 1,2-dichloroethane and 0.1 mL dimethyl formamide was carefully added 4.7 mL (64.4 mmol) of thionyl chloride. The reaction was heated to 90° C. for five hours. The reaction was cooled to room temperature and dry ethyl ether was added. The resulting brown precipitate was collected by vacuum filtration, washed with diethyl ether and dried to afford 2-(7-chloro-thieno[3,2-b]pyridin-2-yl)-4-methyl-thiazole-5-carbonyl chloride (3.31 g) in 78% yield. C12H6Cl2N2OS2: APCI m/z (in methanol to give methyl ester) 325.1/327.1 (pos.); 1H NMR (d6-DMSO): δ 8.68 (d, 1H, J=5.0 Hz), 8.32 (s, 1H), 8.65 (d, 1H, J=5.0 Hz), 2.39 (s, 3H) ppm.

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationThe resulting brown precipitate was collected by vacuum filtration
  3. washwashed with diethyl ether
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-da6df010553b423e9e173a1befebaac2
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06995171B2

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