Triethylamine → 2-(4-Dodecyl-imidazol-1-yl)-2-phenyl-N-(2,4,6-trimethoxy-phenyl)-acetamide

HRID 2380505Notes

Reaction equation

HRID 2380505 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[C:12]=1[NH2:13].[CH2:22]([C:34]1[N:35]=[CH:36][N:37]([CH:39]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:40](O)=[O:41])[CH:38]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1.ClCCl>[CH2:22]([C:34]1[N:35]=[CH:36][N:37]([CH:39]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:40]([NH:13][C:12]2[C:14]([O:20][CH3:21])=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:11]=2[O:10][CH3:9])=[O:41])[CH:38]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 27644342,4,6-trimethoxyaniline HydrochlorideHCID 10642923(+/-)-4-Dodecyl-alpha-phenyl-1H-imidazole-1-acetic acid

Product 1

HCID 106976122-(4-Dodecyl-imidazol-1-yl)-2-phenyl-N-(2,4,6-trimethoxy-phenyl)-acetamideYield 35.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Excess triethylamine (2 mL) was added to a suspension of 2,4,6-trimethoxyaniline hydrochloride (1.6 g, 7.3 mmol) in 500 mL THF and stirred for 1 hour before filtering to remove triethylamine hydrochloride. The filtrate was concentrated and redissolved in 500 mL dichloromethane along with (±)-4-dodecyl-α-phenyl-1H-imidazole-1-acetic acid (2.45 g, 6.6 mmol) at 0° C. Dicyclohexylcarbodiimide (1.43 g, 6.9 mmol) was added in one portion and the resulting suspension was warmed to room temperature and stirred for 16 hours. Filtered to remove a white solid and partitioned the filtrate between dichloromethane and IN HCl. The organic layer was washed with 1N NaOH, dried over MgSO4, filtered, and concentrated. The resulting residue was chromatographed (20% EtOAc/hexanes on silica) to give the title compound as a white solid (1.25 g, 35%); mp 95°-102° C.

Workup

  1. filtrationbefore filtering
  2. customto remove triethylamine hydrochloride
  3. concentrationThe filtrate was concentrated
  4. stirringstirred for 16 hours
  5. filtrationFiltered
  6. customto remove a white solid
  7. custompartitioned the filtrate between dichloromethane
  8. washThe organic layer was washed with 1N NaOH
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe resulting residue was chromatographed (20% EtOAc/hexanes on silica)

Sources & evidence

ORD record
ord-6b1e36350dc5430cbdee3393faae3385
Source dataset
uspto-grants-1994_11
Patent number
US05366987

Reaction notes

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