Water → 9-Octadecynamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-

HRID 371377

反応式

HRID 371377 の反応式
Cl.[OH:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][C:4]=1[O:11][CH3:12].[OH-].[Na+].[C:15](Cl)(=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].O>CN(C)C=O.CCOCC>[CH2:7]([NH:8][C:15](=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[C:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:6]1[CH:9]=[CH:10][C:3]([OH:2])=[C:4]([O:11][CH3:12])[CH:5]=1

参加物

7

反応物 4

HCID 962WaterHCID 8212Stearoyl chlorideHCID 14798Sodium HydroxideHCID 165576Phenol, 4-(aminomethyl)-2-methoxy-, hydrochloride (1:1)

生成物 1

HCID 30245869-Octadecynamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

2.4 g of 4-hydroxy-3-methoxybenzylamine-HCl was suspended in 35 ml of N,N-dimethylformamide (DMF), and stirred. Added were 5 ml of a 5N solution of NaOH, and the mixture was stirred for an additional 10 to 15 minutes. The DMF mixture was chilled in an ice bath, and the stearoyl chloride, prepared above and dissolved in ether, was added dropwise. The mixture was then stirred for 3 hours, allowing it to come to room temperature. The mixture was then poured into 300 ml water, layers separated, and the aqueous layer extracted with ethyl ether. The extracts were washed with HCl, sodium bicarbonate, water, and brine, and then dried and filtered. 5.3 g of crude N-vanillyl-9-octadecynamide was obtained. Purification by recrystallization from toluene and hexane, and then benzene and hexane, gave 2.8 g of analytically pure product. Its structure was confirmed via nuclear magnetic resonance and infrared spectroscopy.

後処理

  1. additionAdded
  2. stirringthe mixture was stirred for an additional 10 to 15 minutes
  3. additionwas added dropwise
  4. stirringThe mixture was then stirred for 3 hours
  5. customto come to room temperature
  6. customseparated
  7. extractionthe aqueous layer extracted with ethyl ether
  8. washThe extracts were washed with HCl, sodium bicarbonate, water, and brine
  9. customdried
  10. filtrationfiltered

出典と根拠

ORDレコード
ord-aa01aae4fdf74e77994208ee264f52ce
出典データセット
uspto-grants-1985_07
特許番号
US04532139

関連ノート

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