Pyridine → HCID 57936378, Verbindung

HRID 219547

Reaktionsgleichung

Reaktionsgleichung von HRID 219547
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[NH:7][C:6]([C:12](Cl)=[O:13])=[CH:5]2.N1C=CC=CC=1.[CH:21]1[C:26]([NH2:27])=[CH:25][CH:24]=[C:23]([S:28]([NH:31][C:32]2[S:36][CH:35]=[CH:34][N:33]=2)(=[O:30])=[O:29])[CH:22]=1>C(Cl)Cl>[S:36]1[CH:35]=[CH:34][N:33]=[C:32]1[NH:31][S:28]([C:23]1[CH:22]=[CH:21][C:26]([NH:27][C:12]([C:6]2[NH:7][C:8]3[C:4]([CH:5]=2)=[CH:3][C:2]([Cl:1])=[CH:10][C:9]=3[Cl:11])=[O:13])=[CH:25][CH:24]=1)(=[O:30])=[O:29]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 5340SulfathiazoleHCID 134663725,7-Dichloro-indole-2-carbonylchloride

Produkt 1

HCID 57936378HCID 57936378, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5,7-dichloro-indole-2-carbonylchloride (186 mg, 0.75 mmol) in pyridine (0.8 mL, 1 mmol) and DCM (5.2 mL) was added N′-(2-thiazolyl)sulfanilamide (128 mg, 0.5 mmol) and the reaction mixture stirred at rt for 16 h. The resulting solid was filtered, washed with DCM (3×5 mL), and dried under vacuum overnight to provide the product (0.21 g; yield=90%) as a white-green solid. 1H-NMR (DMSO-d6) 12.78 (s, 1H), 12.33 (s, 1H), 10.67 (s, 1H), 7.97 (d, J=7.0 Hz, 2H), 7.82 (d, J=7.0 Hz, 2H), 7.62 (d, J=1.5 Hz, 1H), 7.47 (s, 1H), 7.30 (d, J=1.7 Hz, 1H), 7.27 (d, J=4.6 Hz, 1H), 6.84 (d, J=4.6 Hz, 1H). LC/MS (10-99%) M/Z: M+1 obs=467.0; tR=3.12 min.

Aufarbeitung

  1. filtrationThe resulting solid was filtered
  2. washwashed with DCM (3×5 mL)
  3. customdried under vacuum overnight
  4. customto provide the product (0.21 g; yield=90%) as a white-green solid

Quellen und Nachweise

ORD-Eintrag
ord-df5084d69dc7417d97fb4768535dcf5d
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202861B2

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