Acetic Anhydride → N-Benzyl-N-(prop-1-en-1-yl)acetamide

HRID 389263Notes

Reaction equation

HRID 389263 reaction equation
[CH2:1](/[N:8]=[CH:9]/[CH2:10][CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:19](OC(=O)C)(=[O:21])[CH3:20]>>[CH2:1]([N:8](/[CH:9]=[CH:10]/[CH3:11])[C:19](=[O:21])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 178457043HCID 178457043, compound

Product 1

HCID 9942349N-Benzyl-N-(prop-1-en-1-yl)acetamide

Conditions

Temperature
0 °C

Procedure

To benzyl-prop-(E)-ylidene-amine (6.0 g, 40 mmol) in triethylamine (5.67 mL, 40 mmol) at 0° C. was slowly added acetic anhydride (3.81 mL, 40 mmol), and the reaction was stirred for 30 minutes at 0° C. and then overnight at room temperature. The mixture was concentrated, and the residue was purified by silica gel chromatography (0-25% EtOAc in hexanes) to give the title compound.

Workup

  1. customat 0° C.
  2. customovernight
  3. customat room temperature
  4. concentrationThe mixture was concentrated
  5. customthe residue was purified by silica gel chromatography (0-25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-62296e56bb704f65856518b390e5b164
Source dataset
uspto-grants-2013_02
Patent number
US08378107B2

Reaction notes

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