N-Methylacetamide → 1-(N-methylacetamido)-10-undecene

HRID 129893

Reaction equation

HRID 129893 reaction equation
C(N[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19](O)[CH2:20][N:21]([CH3:25])[C:22](=[O:24])[CH3:23])CCCCCCC.[H-].[Na+].BrCCCCCCCCCC=C.CNC(=O)C>CS(C)=O.O>[CH3:25][N:21]([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=[CH2:10])[C:22](=[O:24])[CH3:23]

Participants

7

Reactant 4

HCID 6582N-MethylacetamideHCID 24758Sodium hydrideHCID 28414811-Bromo-1-undeceneHCID 193706641-Octylamino-10-hydroxy-11-(N-methylacetamido)undecane

Product 1

HCID 539229571-(N-methylacetamido)-10-undeceneYield 57%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

This example illustrates a synthesis of 1-Octylamino-10-hydroxy-11-(N-methylacetamido)undecane (compound no. 77). Sodium hydride (0.56 g, 23 mmol) was added to a solution of 1-bromo-10-undecene (5.4 g, 23 mmol) and N-methylacetamide (91.7 g, 23 mmol) in DMSO (40 mL). After 8 hours, the reaction was complete and the mixture added to water (100 mL) and extracted with dichloromethane (3×100 mL). The combined extracts were washed with water (70 mL) and saturated aqueous salt solution (70 mL), and dried over sodium sulfate. The solvent was evaporated under vacuum to give a yellow residue, which was chromatographed (silica/ethyl acetate), yielding 2.95 g of 1-(N-methylacetamido)-10-undecene as a colorless oil (57% yield).

Workup

  1. extractionextracted with dichloromethane (3×100 mL)
  2. washThe combined extracts were washed with water (70 mL) and saturated aqueous salt solution (70 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under vacuum
  5. customto give a yellow residue, which
  6. customwas chromatographed (silica/ethyl acetate)

Sources & evidence

ORD record
ord-22128966178a4921b6df58818b4419ce
Source dataset
uspto-grants-1995_11
Patent number
US05470878

Linked notes

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