Triethylamine → HCID 10012185, compound

HRID 245382Notes

Reaction equation

HRID 245382 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].Cl[C:7](=[O:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9].C(N(CC)CC)C>ClCCl>[CH3:5][O:4][N:3]([CH3:2])[C:7](=[O:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 10012185HCID 10012185, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N,O-dimethylhydroxylamine hydrochloride (10 g, 102.52 mmol) and ethyl chlorooxoacetate (13.77 ml, 123.02 mmol) in dichloromethane (163 ml) at 0° C. was added triethylamine (28.6 ml, 205.04 mmol) drop wise. The reaction was stirred at room temperature for 1.5 hrs. The reaction was quenched with 20 ml of methanol, and then concentrated. The resulting solid was triturated with THF and filtered away. The filtrate was concentrated. The residue was vacuum distilled bulb to bulb. At approximately 85° C. impurities were collected and then discarded. The title compound was collected at approximately 120° C. as a neat oil (11.6 g, 72.0 mmol, 70.2%).

Workup

  1. customThe reaction was quenched with 20 ml of methanol
  2. concentrationconcentrated
  3. customThe resulting solid was triturated with THF
  4. filtrationfiltered away
  5. concentrationThe filtrate was concentrated
  6. distillationdistilled bulb to bulb
  7. customAt approximately 85° C. impurities were collected

Sources & evidence

ORD record
ord-5a580bfcd9dd4ea2a4a2941e5c5caf33
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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