Hydrochloric Acid → Glycine, N-(3-nitrobenzoyl)-

HRID 378113

Reaktionsgleichung

Reaktionsgleichung von HRID 378113
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[OH-].[K+].[N+:8]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14](Cl)=[O:15])([O-:10])=[O:9].Cl.[Na+].[Cl-]>C(#N)C.O>[N+:8]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([NH:1][CH2:2][C:3]([OH:5])=[O:4])=[O:15])([O-:10])=[O:9]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 750GlycineHCID 5234Sodium ChlorideHCID 8495Benzoyl chloride, 3-nitro-HCID 14797Potassium Hydroxide

Produkt 1

HCID 94858Glycine, N-(3-nitrobenzoyl)-Ausbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Glycine (20 g, 266 mmol) was added to water (200 mL), followed by potassium hydroxide (20 g, 357 mmol) and cooled to 0° C. in an ice bath. To this solution was added 3-nitrobenzoyl chloride (20 g, 108 mmol) in acetonitrile (20 mL) drop-wise over a 10 minute period. After the reaction was complete (3-4 hours) concentrated hydrochloric acid was added until pH=2 followed by saturated aqueous NaCl (75 mL). The product was filtered, washed with water and air dried (22 g, 90% yield). 1H-NMR (d6 -DMSO) δ 3.92 (d, 2H, J=6.1), 7.9 (t, 1H, J=7.9), 8.3 (t, 1H, J=5.6), 8.35 (m, 2H), 8.69 (s, 1H), 9.25 (t, 1H, J=7.2 Hz).

Aufarbeitung

  1. additionwas added until pH=2
  2. filtrationThe product was filtered
  3. washwashed with water and air
  4. customdried (22 g, 90% yield)

Quellen und Nachweise

ORD-Eintrag
ord-6437b511a083456b9ca417d762df1447
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06028223

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