Acetic Anhydride → HCID 16762877, compound

HRID 338244Notes

Reaction equation

HRID 338244 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][NH2:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:19](OC(=O)C)(=[O:21])[CH3:20]>C(Cl)Cl.C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][NH:9][C:19](=[O:21])[CH3:20])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 16764930HCID 16764930, compound

Product 1

HCID 16762877HCID 16762877, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-bromophenoxy)ethanamine (500 mg, 2.3 mmol) in CH2Cl2 (20 mL) was added triethylamine (700 mg, 6.9 mmol) and acetic anhydride (470 mg, 4.6 mmol). The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated in vacuo to give a yellow residue. The crude product was diluted with ethyl acetate (20 mL), washed with 1N HCl followed by saturated sodium bicarbonate, dried over sodium sulfate and concentrated in vacuo to give N-[2-(4-bromophenoxy)ethyl]acetamide (400 mg, 67%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.39 (d, 2H), 6.76 (d, 2H), δ 5.89 (m, 1H), 4.00 (m, 2H), 3.67 (m, 2H), δ 2.01 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give a yellow residue
  3. washwashed with 1N HCl
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a81ab296db714633bb753ac4085917a3
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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