Hydrochloric Acid → 5-Methylbenzimidazolone

HRID 501798

Reaktionsgleichung

Reaktionsgleichung von HRID 501798
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1C(O)=O.C([O:15][CH2:16]C)(=O)C.O.Cl.C([N:22](CC)CC)C>O1CCOCC1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>[CH3:11][C:8]1[CH:9]=[CH:10][C:2]2[NH:1][C:16](=[O:15])[NH:22][C:3]=2[CH:7]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 762552-Amino-5-methylbenzoic acid

Produkt 1

HCID 2231345-Methylbenzimidazolone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 312751,4-DioxaneLösungsmittelHCID 199401P,P-Diphenylphosphinic azideLösungsmittel

Versuchsvorschrift

4.00 g of 2-amino-5-methylbenzoic acid was dissolved in 40 mL of 1,4-dioxane, to which 5.5 mL of triethylamine and 6.8 mL of diphenylphosphoryl azide were successively added, and this mixture was stirred for 1.5 hours while heating it under reflux. The reaction mixture, to which a mixture of ethyl acetate and water was added, was adjusted to pH 7 with 1M hydrochloric acid, and the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous sodium sulfate, and the solvent was distilled out under reduced pressure to yield 2.96 g of 5-methyl-1,3-dihydro-2H-benzimidazol-2-one as light yellow solid.

Aufarbeitung

  1. additionwere successively added
  2. temperaturewhile heating it
  3. temperatureunder reflux
  4. additionwas added
  5. customthe organic phase was separated
  6. washAfter the resultant organic phase was washed with water
  7. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled out under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fab17d724e3842a1b89b8960d73c792c
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772285B2

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