Chloroacetic Acid → Glycine, N-(4-nitrophenyl)-

HRID 1373077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1373077
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[CH2:12][C:13]([OH:15])=[O:14]>O>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 300Chloroacetic AcidHCID 74754-Nitroaniline

Produkt 1

HCID 12095Glycine, N-(4-nitrophenyl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a suspension of 4-nitroaniline (13.8 g, 100 mmol) in water (300 mL) was added chloroacetic acid (18.9 g, 200 mmol). The reaction mixture was refluxed overnight and cooled to rt. The title compound was collected by filtration, washed with water and a mixture of hexane and ether (1:1) and dried in vacuo to yield 14.6 g (74%). 1H NMR (400 MHz, DMSO-d6) δ: 12.83 (s, 1H), 8.00 (d, 2H), 7.45 (t, 1H), 6.65 (d, 2H), 4.00 (d, 2H).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed overnight
  2. filtrationThe title compound was collected by filtration
  3. washwashed with water
  4. additiona mixture of hexane and ether (1:1)
  5. customdried in vacuo
  6. customto yield 14.6 g (74%)

Quellen und Nachweise

ORD-Eintrag
ord-7d550b77efa54bcfa87997cf355b8852
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07160902B2

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