Bromoacetyl bromide → N-(4-nitrophenylethyl)bromoacetamide

HRID 36133

Reaktionsgleichung

Reaktionsgleichung von HRID 36133
[Br:1][CH2:2][C:3](Br)=[O:4].[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH2:17])=[CH:11][CH:10]=1)([O-:8])=[O:7]>C(Cl)Cl>[N+:6]([C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][NH:17][C:3](=[O:4])[CH2:2][Br:1])=[CH:13][CH:14]=1)([O-:8])=[O:7]

Komponenten

4

Edukt 2

HCID 61147Bromoacetyl bromideHCID 951534-Nitrophenethylamine

Produkt 1

HCID 54436948N-(4-nitrophenylethyl)bromoacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Bromoacetyl bromide (806 rag, 4.0 mmol) was added dropwise to a solution of p-nitrophenylethylamine (665 mg, 4.0 mmol, freshly prepared from the hydrochloride salt) in 30 mL CH2Cl2 over 6 rain at 0° C. with stirring. Then, the reaction mixture was stirred at 0° C. for 1 h. The resulting precipitate was filtered off and washed twice with 10 mL CH2Cl2, which was combined with filtrate and rotoevaporated to dryness. Chromatography over 20 g silica gel and elution with 5:3 ethyl acetate:hexane gave crystalline N-(4-nitrophenylethyl)bromoacetamide (compound 74) . Recrystallization from ethyl acetate-hexane gave 290 mg (58% yield) of compound 74 as yellow needles: mp 123°-124° C. IR (nujol) 3276, 1659, 1515, 1343 cm-1 ; NMR δ 2.99 (t, 2H), 3.60 (q, 2H), 3.88 (s, 2H), 6.54 (m, 1H), 7 38°-8 20 (AA'BB' 4H) ppm.

Aufarbeitung

  1. stirringThen, the reaction mixture was stirred at 0° C. for 1 h
  2. filtrationThe resulting precipitate was filtered off
  3. washwashed twice with 10 mL CH2Cl2, which
  4. washChromatography over 20 g silica gel and elution with 5:3 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-71ea9eca2eef46919ba2ba8053b5c4f6
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05412148

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