Hydrochloric Acid → HCID 68452512, Verbindung

HRID 2377056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2377056
[NH2:1][C@H:2]([C:9]([OH:11])=[O:10])[CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.[ClH:12].[CH2:13]=O>O>[ClH:12].[ClH:12].[N:8]1[C:4]2[CH2:3][C@@H:2]([C:9]([OH:11])=[O:10])[NH:1][CH2:13][C:5]=2[NH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 178419078HCID 178419078, Verbindung

Produkt 1

HCID 68452512HCID 68452512, VerbindungAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

L-Histidine (204.8 g, 1.32 mol) was added to water (1.2 L) and cooled in an ice/water bath. Concentrated hydrochloric acid (116.0 mL, 1.39 mol, 1.05 mol eq.) was added slowly. Formaldehyde (37 wt/wt % in water, 112.5 g, 1.39 mol, 1.05 mol eq.) was added in one portion. The reaction mixture was stirred for 30 min upon cooling with an ice/water bath, and then refluxed for 75 min. After cooling to room temperature, the solvent was removed under reduced pressure. The residue was suspended in isopropanol (2 L) and HCl (400 mL of a 4 M solution in dioxane) for 30 min. The white solid was filtered and washed with ether. After drying in a vacuum oven (40° C.), the title product was obtained. (313.0 g, 99% yield, 95% pure). 1H NMR (DMSO-d6): 8 ppm 3.05-3.33 (m, 2H), 4.30 (s, 2H), 4.54 (m, 1H), 9.00 (s, 1H), 12.60 (br s, 3H). LCMS: Rt=0.59 min, and M+1=168.1 m/z (M+1 of free base).

Aufarbeitung

  1. temperaturecooled in an ice/water bath
  2. temperatureupon cooling with an ice/water bath
  3. temperaturerefluxed for 75 min
  4. customthe solvent was removed under reduced pressure
  5. waitHCl (400 mL of a 4 M solution in dioxane) for 30 min
  6. filtrationThe white solid was filtered
  7. washwashed with ether
  8. customAfter drying in a vacuum oven (40° C.)

Quellen und Nachweise

ORD-Eintrag
ord-2799d526427a47d4bde68d9123660cb8
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468375B2

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