Acetic Anhydride → N-[1-(4-bromophenyl)ethyl]acetamide

HRID 2170501Notes

Reaction equation

HRID 2170501 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([NH2:17])[CH3:16])=[CH:11][CH:10]=1.[C:18](OC(=O)C)(=[O:20])[CH3:19]>ClCCl>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([NH:17][C:18](=[O:20])[CH3:19])[CH3:16])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 911751-(4-Bromophenyl)ethylamine

Product 1

HCID 2854373N-[1-(4-bromophenyl)ethyl]acetamideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (2.8 mL) was dropped to the solution of 1-(4-bromophenyl)ethanamine (2.0 g, 10.0 mmol), and acetic anhydride (1.53 g, 15.0 mmol) in dichloromethane (30 mL) at room temperature. Then the mixture was stirred at room temperature for 12 hours. The mixture was washed with sodium hydroxide solution (40 mL, 0.5M) and water (40 mL). The organic phase was dried over sodium sulfate and filtered. The filtrate was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=1:5) to give N-(1-(4-bromophenyl)ethyl)acetamide (2.2 g, 91%) as a white solid. 1H NMR (300 MHz, d6-DMSO): δ 8.27 (d, J=4.8 Hz, 1H), 7.38 (d, J=8.4 Hz, 2H), 7.01 (d, J=8.4 Hz, 1H), 4.94 (m, 1H), 2.12 (s, 3H), 1.45 (d, J=6.6 Hz, 3H).

Workup

  1. washThe mixture was washed with sodium hydroxide solution (40 mL, 0.5M) and water (40 mL)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customto give a residue
  6. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=1:5)

Sources & evidence

ORD record
ord-3ba14a6babf54a5bb966048219f8771b
Source dataset
uspto-grants-2015_06
Patent number
US09051269B2

Reaction notes

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