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Butyric Acid → 4-Methyl-2-propyl-1H-benzimidazole

HRID 1977827
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1977827
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].[C:10](O)(=O)[CH2:11][CH2:12][CH3:13].[H-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].C(=O)=O>O>[CH3:9][C:3]1[C:2]2[N:1]=[C:10]([CH2:11][CH2:12][CH3:13])[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 264Butyric AcidHCID 280Carbon DioxideHCID 10340Sodium CarbonateHCID 175932,3-DiaminotolueneHCID 24758Sodium hydride

Produkt 1

HCID 219956454-Methyl-2-propyl-1H-benzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

5.00 g (41 mmol) of 2,3-diamino-toluene and 3.7 ml (41 mmol) of butyric acid are stirred in 41 ml of polyphosphoric acid at 120° C. for 3 hours, and the mixture is poured into 410 ml of water and brought to pH=9 with solid sodium hydride. Thereafter, sodium carbonate is added until the evolution of carbon dioxide has ended, the mixture is extracted five times with 100 ml of ethyl acetate each time, the combined organic phases are dried with anhydrous sodium sulphate and the solution is evaporated—finally under a high vacuum; crude weight: 5.89 g. The product is purified by chromatography over silica gel 60 (Merck/40-63 μm/methylene chloride:methanol=100:1); yield: 2.45 (34%). Rf=0.16 (methylene chloride:methanol=20:1)

Aufarbeitung

  1. extractionthe mixture is extracted five times with 100 ml of ethyl acetate each time
  2. dry with materialthe combined organic phases are dried with anhydrous sodium sulphate
  3. customthe solution is evaporated—finally under a high vacuum
  4. customThe product is purified by chromatography over silica gel 60 (Merck/40-63 μm/methylene chloride:methanol=100:1)

Quellen und Nachweise

ORD-Eintrag
ord-201323a010e24d32aa29cc9a4b2b9ce3
Quelldatensatz
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06235770B1

Notizen zur Reaktion

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