Bromoacetyl bromide → N-(4-nitrophenylethyl)bromoacetamide

HRID 846024Notes

Reaction equation

HRID 846024 reaction equation
[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]

Participants

4

Reactant 2

HCID 61147Bromoacetyl bromideHCID 951534-Nitrophenethylamine

Product 1

HCID 54436948N-(4-nitrophenylethyl)bromoacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromoacetyl bromide (806 mg, 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 min 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 tiltrate 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.

Workup

  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

Sources & evidence

ORD record
ord-3eaddd31bdb04b20a7bfa843b545f625
Source dataset
uspto-grants-1992_08
Patent number
US05135737

Reaction notes

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