Triethylamine → N,2-dimethoxy-N-methylacetamide

HRID 1260587Notes

Reaction equation

HRID 1260587 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][CH2:10][C:11](Cl)=[O:12].Cl.[CH3:15][NH:16][O:17][CH3:18]>ClCCl>[CH3:18][O:17][N:16]([CH3:15])[C:11](=[O:12])[CH2:10][O:9][CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 96623Methoxyacetyl chloride

Product 1

HCID 14872187N,2-dimethoxy-N-methylacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

35.96 ml of triethylamine (258 mmol), followed by a solution of 14 g of methoxyacetyl chloride (Aldrich, 129 mmol) in 250 ml of dichloromethane, are added to a solution of N-methyl-O-methylhydroxylamine hydrochloride in 250 ml of dichloromethane cooled to 0° C. The mixture is stirred for 3 hours while allowing it to return to ambient temperature. A 1N solution of HClaq is added and then the organic phase is washed with water, dried over sodium sulphate, filtered, and concentrated under vacuum. 13.14 g of expected product are obtained in the form of an oil which is used without subsequent purification (crude yield=76%).

Workup

  1. customto return to ambient temperature
  2. washthe organic phase is washed with water
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a2cb572a4bfa43ab8ecc68509c06188d
Source dataset
uspto-grants-2013_06
Patent number
US08470847B2

Reaction notes

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