1,1'-Carbonyldiimidazole → 3-Methoxy-4,5-dimethy-N-1H-tetrazol-5-yl-2-thiophenecarboxamide

HRID 621796Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 621796
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][O:14][C:15]1[C:19]([CH3:20])=[C:18]([CH3:21])[S:17][C:16]=1[C:22]([OH:24])=O.[NH2:25][C:26]1[NH:30][N:29]=[N:28][N:27]=1>O1CCCC1>[CH3:13][O:14][C:15]1[C:19]([CH3:20])=[C:18]([CH3:21])[S:17][C:16]=1[C:22]([NH:25][C:26]1[NH:30][N:29]=[N:28][N:27]=1)=[O:24]

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 13061858HCID 13061858, VerbindungHCID 178509299HCID 178509299, Verbindung

Produkt 1

HCID 1784935763-Methoxy-4,5-dimethy-N-1H-tetrazol-5-yl-2-thiophenecarboxamideAusbeute 72,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1,1'-Carbonyldiimidazole (4.1 g, 25 mmoles) is added to a solution of 3-methoxy-4,5-dimethyl-2-thiophenecarboxylic acid (4.5 g, 24 mmoles) in tetrahydrofuran (80 mL) under argon. The mixture is stirred and heated under reflux for 1.5 hours. 5-Aminotetrazole (2.0 g, 24 mmoles) is added and heating under reflux is continued for an additional 2.5 hours. The mixture is cooled, and the precipitate is filtered off, rinsed with tetrahydrofuran, dried, and stirred in 2N HCl. After 10 minutes the suspended solid is collected by filtration, rinsed with water and dried to afford the product (4.4 g); mp 229° C. (dec).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureheating
  4. temperatureunder reflux
  5. temperatureThe mixture is cooled
  6. filtrationthe precipitate is filtered off
  7. washrinsed with tetrahydrofuran
  8. customdried
  9. stirringstirred in 2N HCl
  10. filtrationAfter 10 minutes the suspended solid is collected by filtration
  11. washrinsed with water
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5941bea248584bf2a40073fb2af84824
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04824958

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