Imidazole → 1-(18-(benzyloxy)octadecan-9-yl)-1H-imidazole

HRID 2204038ノート

反応式

HRID 2204038 の反応式
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18](O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(Cl)(=O)=O.[NH:33]1[CH:37]=[CH:36][N:35]=[CH:34]1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([N:33]1[CH:37]=[CH:36][N:35]=[CH:34]1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 795ImidazoleHCID 31297Methanesulfonyl chlorideHCID 8669165218-(Benzyloxy)octadecan-9-ol

生成物 1

HCID 866916531-(18-(benzyloxy)octadecan-9-yl)-1H-imidazole収率 33%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

18-(benzyloxy)octadecan-9-ol (6 g, 15.93 mmol), DMAP (0.195 g, 1.59 mmol) and TEA (2.9 ml, 20.71 mmol) in dry DCM (90 ml) were cooled to 0° C., then methanesulfonyl chloride (1.64 ml) was added under N2. The reaction was warmed to room temperature and stirring continued for another 3 h. The reaction mixture was diluted with DCM (100 ml), washed with 1N HCl, water, and brine solution and dried over MgSO4. The crude compound and imidazole (2.17 g, 31.86 mmol) were then heated at 70° C. for 16 h. The crude product was purified by silica gel column (1.5% MeOH in DCM) to give 1-(18-(benzyloxy)octadecan-9-yl)-1H-imidazole as a gummy liquid (2.22 g, 33%).

後処理

  1. washwashed with 1N HCl, water, and brine solution
  2. dry with materialdried over MgSO4
  3. customThe crude product was purified by silica gel column (1.5% MeOH in DCM)

出典と根拠

ORDレコード
ord-c3f8ea23497f496098a1c2b5e6308cf8
出典データセット
uspto-grants-2016_06
特許番号
US09365597B2

反応ノート

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