Ammonia → 12-Methoxydodecanamide

HRID 618306Notes

Reaction equation

HRID 618306 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-c1b6fafd997a465e86978c6895a793a3
Source dataset
uspto-grants-1999_09
Patent number
US05952377

Reaction notes

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