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

HRID 2204038노트

반응식

HRID 2204038 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-c3f8ea23497f496098a1c2b5e6308cf8
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365597B2

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