Tetrahydrofuran → 5-Methylbenzimidazolone

HRID 1096657

Reaktionsgleichung

Reaktionsgleichung von HRID 1096657
[NH2:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[CH:6][C:7]=1[NH2:8].C1C[O:13][CH2:12]C1>>[CH3:9][C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:12](=[O:13])[NH:1][C:2]=2[CH:3]=1

Komponenten

3

Edukt 2

HCID 8028Tetrahydrofuran2×HCID 103323,4-Diaminotoluene

Produkt 1

HCID 2231345-MethylbenzimidazoloneAusbeute 82 %

Versuchsvorschrift

Into a 100 mL round bottomed flask, 3,4-diaminotoluene (1.00 g, 8.2 mmol) was dissolved in THF (8.2 mL). CDT (1.59 g, 9.8 mmol) in THF (25 mL) was added slowly via addition funnel. After addition the mixture was stirred overnight at room temperature. Solvent was removed under vacuum and the residue was purified by column chromatography (5% MeOH/DCM) to give the product 5-methyl-1H-benzo[d]imidazol-2(3H)-one (110A) as a brown-tan solid (990 mg, 82% yield). ESI-MS:m/z 149.4 (M+H)+.

Aufarbeitung

  1. additionAfter addition the mixture
  2. customSolvent was removed under vacuum
  3. customthe residue was purified by column chromatography (5% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-04d014e3941942008cb6a4d14632d73e
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138168B1

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