Pyridine → HCID 178474481, Verbindung

HRID 1655039

Reaktionsgleichung

Reaktionsgleichung von HRID 1655039
N1C=CC=CC=1.[Cl:7][C:8]1[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]([Cl:16])[C:9]=1[NH2:10].[C:17]([NH:20][C:21]1[NH:25][N:24]=[C:23]([S:26](Cl)(=[O:28])=[O:27])[N:22]=1)(=[O:19])[CH3:18].[OH-].[Na+]>C(Cl)Cl>[Cl:7][C:8]1[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]([Cl:16])[C:9]=1[NH:10][S:26]([C:23]1[N:22]=[C:21]([NH:20][C:17](=[O:19])[CH3:18])[NH:25][N:24]=1)(=[O:27])=[O:28]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 1165292,6-Dichloro-3-methylanilineHCID 178474479HCID 178474479, Verbindung

Produkt 1

HCID 178474481HCID 178474481, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 250 ml, 1-necked flask equipped with a magnetic stirrer and filled with nitrogen gas was charged with 15 ml of dry pyridine and 8.8 g (0.05 mole) of 2,6-dichloro-3-methylaniline. To the stirred solution was added 11.3 g (0.05 mole) of crude 5-acetylamino-3-chlorosulfonyl-1,2,4-triazole over 10-30 minutes. The resulting dark green mixture, which had a mild exotherm during the addition, was heated to 100°-105° C. with stirring for 3-4 hours. It was then dispersed between a mixture of methylene chloride and dilute aqueous sodium hydroxide and the organic layer was removed. Acidification of the aqueous phase and filtraton and drying of the precipitate that formed gave the title sulfonamide as a tan solid melting at 284° (dec.). The yield was 60 percent of theory. A sample of this compound which was recrystallized from a mixture of methanol and water was a pale ivory powder melting at 285°-285.5° C. (dec.) and had the following elemental analysis:

Aufarbeitung

  1. customA 250 ml, 1-necked flask equipped with a magnetic stirrer
  2. additionfilled with nitrogen gas
  3. additionduring the addition
  4. temperaturewas heated to 100°-105° C.
  5. customthe organic layer was removed
  6. customAcidification of the aqueous phase and filtraton and drying of the precipitate
  7. customthat formed

Quellen und Nachweise

ORD-Eintrag
ord-2f7eaaaa7d0f4cad94439dfe48975a03
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05410065

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