Imidazole → HCID 86691644, compound

HRID 2204029Notes

Reaction equation

HRID 2204029 reaction equation
O[CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:3][C:4]#[N:5].CS(Cl)(=O)=O.[NH:26]1[CH:30]=[CH:29][N:28]=[CH:27]1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[N:26]1([CH:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:2][CH2:3][C:4]#[N:5])[CH:30]=[CH:29][N:28]=[CH:27]1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 31297Methanesulfonyl chlorideHCID 86691645HCID 86691645, compound

Product 1

HCID 86691644HCID 86691644, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of β-hydroxyoctadecanenitrile (4.5 g, 15.99 mmol), TEA (2.9 ml, 20.78 mmol) and DMAP (0.19 g, 1.59 mmol) in dry DCM (70 ml) cooled to 0° C., was added methanesulfonyl chloride (1.3 ml, 16.78 mmol) under N2. After allowing the reaction mixture to warm to room temperature, stirring was continued for another 2 hours. The reaction mixture was diluted with DCM (100 ml), the organic layer was washed with 1N HCl, water and brine solution, dried over MgSO4 and concentrated under reduced pressure. This crude compound was mixed with imidazole (2.18 g, 31.97 mmol) and heated at 70° C. for 16 hours under N2. The crude product was purified by silica gel column (2% MeOH in DCM) to give 13-(1H-imidazol-1-yl)octadecanenitrile as a light yellow liquid (1.64 g, 32%).

Workup

  1. washthe organic layer was washed with 1N HCl, water and brine solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. temperatureheated at 70° C. for 16 hours under N2
  5. customThe crude product was purified by silica gel column (2% MeOH in DCM)

Sources & evidence

ORD record
ord-656607b1b87c4a3c981e33b45c90e490
Source dataset
uspto-grants-2016_06
Patent number
US09365597B2

Reaction notes

Loading…