Hydrochloric Acid → HCID 67282269, Verbindung

HRID 1253818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1253818
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([N+:11]([O-])=O)[CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:14]([F:17])([F:16])[F:15].Cl.Cl[Sn](Cl)(Cl)Cl.[OH-].[Na+]>O>[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([NH2:11])[CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:14]([F:16])([F:15])[F:17]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 67283381HCID 67283381, Verbindung

Produkt 1

HCID 67282269HCID 67282269, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A 250 ml round bottomed flask was charged with 1-methyl-6-nitro-2-(trifluoromethyl)-1H-benzo[d]imidazole (6 g, 24 mmol) and concentrated HCl (40 ml). Once the solution has become clear, water (˜15 ml) was added until the solution just started to become cloudy. SnCl4 (27 g, 120 mmol) was added in portions over 5 minutes (caution exotherm!). Initial exotherm caused the temperature to rise to 60° C. The reaction mixture was stirred and allowed to cool down to room temperature. After 1 hour, the reaction mixture was diluted with water (100 ml), basified with 1M NaOH and extracted twice with ethyl acetate. The organic layers were combined, washed with brine, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a dark coloured solid. (5 g, 100% yield). 1H NMR (DMSO D6, 400 MHz) 3.75 (3H, s), 4.6 (2H, br s), 6.65 (1H, s), 6.7 (1H, d), 7.75 (1H, d); MS (ES+) 215.

Aufarbeitung

  1. customto rise to 60° C
  2. extractionextracted twice with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a8a670350ea04957b29ae28179b40859
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455507B2

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