Imidazole → HCID 86691638, compound

HRID 2204022Notes

Reaction equation

HRID 2204022 reaction equation
CS(Cl)(=O)=O.O[CH:7]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13].C(N(CC)CC)C.[NH:35]1[CH:39]=[CH:38][N:37]=[CH:36]1>ClCCl>[N:35]1([CH:7]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:39]=[CH:38][N:37]=[CH:36]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 559013Methyl 6-hydroxyoctadecanoate

Product 1

HCID 86691638HCID 86691638, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.39 ml, 4.99 mmol) was added dropwise to a stirred solution of methyl 6-hydroxyoctadecanoate (1.55 g, 4.94 mmol) and triethylamine (0.89 ml, 6.42 mmol) in dry dichloromethane (30 ml) at 0° C. The reaction mixture was warmed to room temperature after the addition, and stirred for 2 h. The reaction mixture was quenched with water, diluted with 50 ml of dichloromethane, and the organic layer was washed with water and brine solution, dried on anhydrous MgSO4, concentrated and evaporated under vacuum. This crude compound was combined with imidazole (0.67 g, 9.88 mmol) and heated at 80° C. for 16 h. Crude compound was purified on silica gel (2% methanol in dichloromethane) to obtain a light brown liquid (605 mg, 33.7%).

Workup

  1. additionafter the addition
  2. customThe reaction mixture was quenched with water
  3. additiondiluted with 50 ml of dichloromethane
  4. washthe organic layer was washed with water and brine solution
  5. dry with materialdried on anhydrous MgSO4
  6. concentrationconcentrated
  7. customevaporated under vacuum
  8. temperatureheated at 80° C. for 16 h
  9. customCrude compound was purified on silica gel (2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-5fe086e759374fed9f574adf8dc45a35
Source dataset
uspto-grants-2016_06
Patent number
US09365597B2

Reaction notes

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