Pyridine → HCID 18376557, Verbindung

HRID 370075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 370075
[Cl:1][C:2]1[C:6]([CH2:7][Cl:8])=[CH:5][S:4][C:3]=1[C:9](Cl)=[O:10].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:29])[C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=2[NH2:28])=[CH:15][CH:14]=1.N1C=CC=CC=1>C(Cl)Cl>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([NH:19][C:20](=[O:29])[C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=2[NH:28][C:9]([C:3]2[S:4][CH:5]=[C:6]([CH2:7][Cl:8])[C:2]=2[Cl:1])=[O:10])=[CH:17][CH:18]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 41860192-amino-5-chloro-N-(4-chlorophenyl)benzamideHCID 183766763-Chloro-4-chloromethyl-2-(chlorocarbonyl)thiophene

Produkt 1

HCID 18376557HCID 18376557, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-chloro-4-chloromethyl-2-(chlorocarbonyl)thiophene (3.1 g, 13.5 mmol) in methylene chloride (40 mL) at 0° C. was added N-(4-chlorophenyl)-2-amino-5-chlorobenzamide (3.8 g, 13.5 mmol), followed after 5 minutes by pyridine (1.6 mL, 16 mmol). The mixture was warmed to ambient temperature. After 17 hours, the mixture was concentrated of all volatiles in vacuo. The resulting solid was triturated with water and a small amount of acetonitrile and dried in vacuo to afford 5.1 g (80% yield) of N-(4-chlorophenyl)-2-[((4-(chloromethyl)-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide as a tan powder: NMR (DMSO-d6) 11.1 (s, 1), 10.8 (s, 1), 8.3 (d, 1), 8.2 (s, 1), 7.9 (s, 1), 7.7 (d, 2), 7.6 (dd, 1), 7.4 (d, 2), 4.8 (s, 2) ppm.

Aufarbeitung

  1. concentrationthe mixture was concentrated of all volatiles in vacuo
  2. customThe resulting solid was triturated with water
  3. dry with materiala small amount of acetonitrile and dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-59e6d36c5cf741ff976e42886025cd67
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06140351

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