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

HRID 129893

반응식

HRID 129893 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-22128966178a4921b6df58818b4419ce
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05470878

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