Imidazole → HCID 86691650, compound

HRID 2204034Notes

Reaction equation

HRID 2204034 reaction equation
O[CH:2]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16].CS(Cl)(=O)=O.[NH:34]1[CH:38]=[CH:37][N:36]=[CH:35]1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[N:34]1([CH:2]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:38]=[CH:37][N:36]=[CH:35]1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 31297Methanesulfonyl chlorideHCID 86691649HCID 86691649, compound

Product 1

HCID 86691650HCID 86691650, compoundYield 32.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Diethyl 2-(12-hydroxyhexadecyl)malonate (1.75 g, 4.369 mmol), TEA (0.79 ml, 5.679 mmol) and DMAP (53 mg, 0.437 mmol) were dissolved in dry DCM (20 ml), cooled to 0° C., then methane sulfonyl chloride (0.36 ml, 4.587 mmol) was slowly added. The ice bath was removed, and stirring continued for another 2 h at room temperature. The reaction mixture was diluted with DCM (75 ml), washed with water (50 ml), 0.5 N HCl (10 ml) and brine solution (20 ml), dried on dry MgSO4 and concentrated. The crude compound was mixed with imidazole (595 mg, 8.737 mmol) and stirred at 75° C. for 16 h. The crude compound was purified by silica gel column (2% MeOH in DCM) to give diethyl 2-(12-(1H-imidazol-1-yl)hexadecyl)malonate (640 mg, 32.5%) as a light brown coloured liquid.

Workup

  1. customThe ice bath was removed
  2. additionThe reaction mixture was diluted with DCM (75 ml)
  3. washwashed with water (50 ml), 0.5 N HCl (10 ml) and brine solution (20 ml)
  4. dry with materialdried on dry MgSO4
  5. concentrationconcentrated
  6. stirringstirred at 75° C. for 16 h
  7. customThe crude compound was purified by silica gel column (2% MeOH in DCM)

Sources & evidence

ORD record
ord-4db931160f494e3f9ea816a78403f9ad
Source dataset
uspto-grants-2016_06
Patent number
US09365597B2

Reaction notes

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