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

HRID 129893

反応式

HRID 129893 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 539229571-(N-methylacetamido)-10-undecene収率 57%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-22128966178a4921b6df58818b4419ce
出典データセット
uspto-grants-1995_11
特許番号
US05470878

関連ノート

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