Ammonium Chloride → 5-Chloro-2-(1H-tetrazol-1-YL)benzamide

HRID 857716Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857716
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:11]2[CH:15]=[N:14][N:13]=[N:12]2)=[C:6]([CH:10]=1)[C:7](O)=[O:8].[Cl-].[NH4+].Cl.C[N:20](C)CCCN=C=NCC.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:11]2[CH:15]=[N:14][N:13]=[N:12]2)=[C:6]([CH:10]=1)[C:7]([NH2:20])=[O:8]

Komponenten

8

Edukt 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 117155615-Chloro-2-(1H-tetrazol-1-yl)benzoic acid

Produkt 1

HCID 218661695-Chloro-2-(1H-tetrazol-1-YL)benzamideAusbeute 115,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 5-chloro-2-(1H-tetraazol-1-yl)benzoic acid (2.0 g, 8.9 mmol), ammonium chloride (0.95 g, 17.8 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.4 g, 17.8 mmol), HOAt (2.4 g, 17.8 mmol) and DIEA (6.2 mL, 35.6 mmol) in DMF (26 mL) was stirred at room temperature overnight. Water was added and the reaction mixture was extracted with ethyl acetate. The combined organic layers were washed with brine. Drying and solvent evaporation gave 5-chloro-2-(1H-tetrazol-1-yl)benzamide (2.3 g); 1H NMR (400 MHz, CD3OD): δ 9.44 (s, 1H), 7.82 (d, J=2.3 Hz, 1H), 7.75 (dd, J=2.3, 8.5 Hz, 1H), 7.66 (d, J=8.5 Hz, 1H).

Aufarbeitung

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. customDrying
  4. customsolvent evaporation

Quellen und Nachweise

ORD-Eintrag
ord-4378230f23de4082ad5559dd767b7bbd
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144899B2

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