Acetic Anhydride → HCID 16762877, compound

HRID 1054587Notes

Reaction equation

HRID 1054587 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 1 N 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, 2 H), 6.76 (d, 2 H), δ 5.89 (m, 1 H), 4.00 (m, 2 H), 3.67 (m, 2 H), δ 2.01 (s, 3 H).

Workup

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

Sources & evidence

ORD record
ord-85b5baac6ab342df8b78fee018a57fb4
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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