Diethylamine → 2-bromo-N,N-diethylacetamide

HRID 1458956Notes

Reaction equation

HRID 1458956 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[Br:6][CH2:7][C:8](Br)=[O:9]>ClCl.C(Cl)Cl>[CH2:1]([N:3]([CH2:4][CH3:5])[C:8](=[O:9])[CH2:7][Br:6])[CH3:2]

Participants

5

Reactant 2

HCID 8021DiethylamineHCID 61147Bromoacetyl bromide

Product 1

HCID 2255452-bromo-N,N-diethylacetamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24526ChlorineSolvent

Procedure

N,N-diethylbromoacetamide was prepared as follows: Diethylamine (1.54 mL, 14.9 mmol) and TEA (2.49 mL, 17.9 mmol) were dissolved in 75 mL CH2 Cl2, then bromoacetyl bromide (1.29 mL, 14.9 mmol) was added dropwise. After 2 h, the reaction was diluted with CH2Cl2, washed with water (2×), and brine, dried (MgSO4), filtered and concentrated. Flash chromatography (silica, 45% EtOAc/hexanes) provided N,N-diethylbromoacetamide as a lachrymatory yellow oil.

Workup

  1. customN,N-diethylbromoacetamide was prepared
  2. washwashed with water (2×), and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-64e4f1572b8944868e418dfc33a63efd
Source dataset
uspto-grants-1998_12
Patent number
US05852045

Reaction notes

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