Acetyl chloride → N-(2,2-Dimethoxyethyl)acetamide

HRID 2047628Notes

Reaction equation

HRID 2047628 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(OCC)(=O)C.[CH3:11][O:12][CH:13]([O:16][CH3:17])[CH2:14][NH2:15].C(N(CC)CC)C>C(O)C>[CH3:11][O:12][CH:13]([O:16][CH3:17])[CH2:14][NH:15][C:1](=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 15289457N-(2,2-Dimethoxyethyl)acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8.2 mL of acetyl chloride were added to a solution of 150 ml of ethyl acetate, 11.2 mL of 2,2-dimethoxyethanamine and 21 mL of triethyl amine at room temperature. After 1 hour, 1.5 mL of ethanol were added. The resulting suspension was stirred for a further hour, and then filtered. Ethyl acetate was removed by evaporation from the filtration liquors yielding the title compound as an oil, which was used without further purifications . H1-NMR (DMSOd6), δ ppm: 7.85 (s broad, 1H); 4.30 (t; 1H); 3.25 (s, 6H); 3.10 (t, 2H); 1.80 (s, 3H).

Workup

  1. filtrationfiltered
  2. customEthyl acetate was removed by evaporation from the filtration liquors

Sources & evidence

ORD record
ord-6ddd4dcf540d475d94acc45f743c4d05
Source dataset
uspto-grants-2013_11
Patent number
US08592583B2

Reaction notes

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