Methyl iodide → Methyl 1-methyl-1H-benzo[d]imidazole-5-carboxylate

HRID 1051542

Reaktionsgleichung

Reaktionsgleichung von HRID 1051542
[NH:1]1[C:5]2[CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[H-].[Na+].CI.[CH3:18]N1C2C=C(C(OC)=O)C=CC=2N=C1>C1COCC1>[CH3:18][N:3]1[C:4]2[CH:9]=[CH:8][C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:6][C:5]=2[N:1]=[CH:2]1

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2779733methyl 1H-1,3-benzodiazole-5-carboxylateHCID 10583823Methyl 1-methyl-1H-benzo[d]imidazole-6-carboxylate

Produkt 1

HCID 965319Methyl 1-methyl-1H-benzo[d]imidazole-5-carboxylateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of methyl 1H-benzo[d]imidazole-6-carboxylate (9.5 g, 53.9 mmol) in THF (100 mL) had NaH (2.59 g, 64.7 mmol) added at 0° C. After stirring for 30 min, CH3I (13.23 g, 93.2 mmol) was added and the mixture was stirred at room temperature for 1 h. The reaction was then quenched by addition of water and extracted with DCM (3×100 mL). The combined organic layers were dried over Na2SO4 and concentrated to give a mixture of two isomeric products methyl 1-methyl-1H-benzo[d]imidazole-6-carboxylate and methyl 1-methyl-1H-benzo[d]imidazole-5-carboxylate (8.0 g, Yield 78%). LCMS (m/z): 191.06 (M+1). This crude mixture was used directly in the next step.

Aufarbeitung

  1. additionadded at 0° C
  2. stirringthe mixture was stirred at room temperature for 1 h
  3. customThe reaction was then quenched by addition of water
  4. extractionextracted with DCM (3×100 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated
  7. customto give

Quellen und Nachweise

ORD-Eintrag
ord-095faa01399a4735bfb4e66fe47b0307
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388173B2

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