Ammonia → 12-Methoxydodecanamide

HRID 1602476Notes

Reaction equation

HRID 1602476 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](Cl)=[O:15].[NH3:17]>O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH2:17])=[O:15]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 1961175912-Methoxydodecanoyl chloride

Product 1

HCID 983750412-Methoxydodecanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the title product from Example 11 (1.1 g, 4.3 mmol) in 70 mL of anhydrous tetrahydrofuran was added 20 mL of freshly distilled liquid ammonia in a Parr shaker which was sealed and shaken at room temperature for 16 hours. After filtering and concentration, the crude residue was dissolved in anhydrous methanol and passed through a basic ion exchange resin and eluted with anhydrous methanol. Concentration afforded the title compound (780 mg) as a white solid, m.p. 83.9-85.6° C. (DSC). The structure was supported by NMR, infrared spectroscopy, elemental analysis, and mass spectroscopy.

Workup

  1. customwas sealed
  2. filtrationAfter filtering
  3. concentrationconcentration
  4. dissolutionthe crude residue was dissolved in anhydrous methanol
  5. washeluted with anhydrous methanol
  6. concentrationConcentration

Sources & evidence

ORD record
ord-2454e4867c3e42aba6feb9c5599c5cc2
Source dataset
uspto-grants-1999_11
Patent number
US05981580

Reaction notes

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