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

HRID 2204038Notes

Reaction equation

HRID 2204038 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-c3f8ea23497f496098a1c2b5e6308cf8
Source dataset
uspto-grants-2016_06
Patent number
US09365597B2

Reaction notes

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