Allyl bromide → N-Octadecyl-N-[(prop-2-en-1-yl)oxy]octadecan-1-amine

HRID 727986ノート

反応式

HRID 727986 の反応式
[CH2:1]([N:19]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[OH:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH2:39](Br)[CH:40]=[CH2:41].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C(Cl)(Cl)Cl>[CH2:41]([O:20][N:19]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH:40]=[CH2:39]

参加物

6

反応物 3

HCID 7841Allyl bromideHCID 10340Sodium CarbonateHCID 3507778Bis(octadecyl)hydroxylamine2 回

生成物 1

HCID 21885151N-Octadecyl-N-[(prop-2-en-1-yl)oxy]octadecan-1-amine収率 36%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6212Chloroform溶媒

実験手順

A mixture of 42.4 g (80 mmol) of N,N-dioctadecylhydroxylamine, 13 ml (150 mmol) of allyl bromide and 17.0 g (160 mmol) of sodium carbonate in 450 ml of ethanol is heated under reflux at approximately 80° to 85° C. The reaction is considered complete after 14 hours upon complete disappearance of the N,N-dioctadecylhydroxylamine as indicated by TLC analysis (silica gel, chloroform solvent). The reaction mixture is concentrated under reduced pressure and the resultant residue is triturated with 500 ml of chloroform. The insoluble salts are removed by filtration and the filtrate concentrated. The resultant residue is purified by flash chromatography (silica gel, chloroform solvent) to give 16.6 g (36% yield) of the title compound as a white solid melting at 60°-62° C.

後処理

  1. temperatureis heated
  2. temperatureunder reflux at approximately 80° to 85° C
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. customthe resultant residue is triturated with 500 ml of chloroform
  5. customThe insoluble salts are removed by filtration
  6. concentrationthe filtrate concentrated
  7. customThe resultant residue is purified by flash chromatography (silica gel, chloroform solvent)

出典と根拠

ORDレコード
ord-a966b0288b924ca387cdec9925132118
出典データセット
uspto-grants-1991_09
特許番号
US05045583

反応ノート

読み込み中…