Thionyl Chloride → 2-Bromoimidazo[2,1-b]thiazole-6-carbonyl azide

HRID 1811663Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1811663
S(Cl)(Cl)=O.[Br:5][C:6]1[S:10][C:9]2=[N:11][C:12]([C:14]([OH:16])=O)=[CH:13][N:8]2[CH:7]=1.[N-:17]=[N+:18]=[N-:19].[Na+]>O>[Br:5][C:6]1[S:10][C:9]2=[N:11][C:12]([C:14]([N:17]=[N+:18]=[N-:19])=[O:16])=[CH:13][N:8]2[CH:7]=1

Komponenten

5

Edukt 3

HCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 127446152-Bromoimidazo[2,1-b]thiazole-6-carboxylic acid

Produkt 1

HCID 583102352-Bromoimidazo[2,1-b]thiazole-6-carbonyl azideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Thionyl chloride (0.33 mol) was added to 2-bromoimidazo[2,1-b]thiazole-6-carboxylic acid (13.1 mmol). The reaction mixture was stirred at 85° C. during 3 hrs. The mixture was then concentrated under vacuum and the residue was taken in acetone (40 mL). The sodium azide (14.4 mmol) in water (5.2 mL) was added in one portion at 0° C. and the mixture was stirred at 0-10° C. for 45 min. Water was added, and the solid filtered off and washed with water and then with a mixture of water/acetone (50/50). The solid was dried in vacuo to give compound 9 as a beige solid in 80% yield. 1H NMR (DMSO-d6, 400 MHz) δ (ppm) 8.27 (s, 1H), 8.49 (s, 1H); and MS (ESI, EI+) m/z=272.05-274.07 (MH+).

Aufarbeitung

  1. concentrationThe mixture was then concentrated under vacuum
  2. stirringthe mixture was stirred at 0-10° C. for 45 min
  3. filtrationthe solid filtered off
  4. washwashed with water
  5. additionwith a mixture of water/acetone (50/50)
  6. customThe solid was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f749052f050a4515ac12a7c97cdbf699
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362068B2

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