Formic Acid → HCID 66987301, Verbindung

HRID 555273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 555273
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][OH:13])=[C:6]([NH2:14])[CH:5]=1.[CH:16](O)=O>>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([CH2:11][CH2:12][OH:13])[CH:16]=[N:14][C:6]=2[CH:5]=1)=[O:15]

Komponenten

3

Edukt 2

HCID 284Formic Acid2×HCID 51358181HCID 51358181, Verbindung

Produkt 1

HCID 66987301HCID 66987301, VerbindungAusbeute 78 %

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

3-Amino-4-(2-hydroxy-ethylamino)-benzoic acid methyl ester (2.6 g, 12.0 mmol) was dissolved in formic acid (20 mL). The solution was heated at 45° C. for 1 h. After checking the completion of reaction by TLC, formic acid was evaporated at <40° C. under reduced pressure and the resulting solid was recrystallized from EtOAc. The above solid was dissolved in 3N HCl, stirred at ambient temperature for 1 h, basified back with saturated sodium bicarbonate solution and extracted with EtOAc. The organic layer was evaporated to give 2.1 g (78%) of 1-(2-hydroxy-ethyl)-1H-benzoimidazole-5-carboxylic acid methyl ester. MS-ESI m/z 221 (M+1): 1H NMR (300 MHz, DMSO-d6) δ 3.7 (q, 2H), 3.9 (s, 3H), 4.3 (t, 3H), 5.0 (t, 1H), 7.7 (d, 1H), 7.9 (dd, 1H), 8.25 (s, 1H), 8.35 (s, 1H)

Aufarbeitung

  1. customwas evaporated at <40° C. under reduced pressure
  2. customthe resulting solid was recrystallized from EtOAc
  3. dissolutionThe above solid was dissolved in 3N HCl
  4. extractionextracted with EtOAc
  5. customThe organic layer was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-6344907218d44c418049a5ed578ea07f
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053431B2

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