Pyridine → N-[4-(2-methyl-1H-imidazol-1-yl)phenyl]-4-(tetradecyloxy)benzeneacetamide

HRID 483574Notes

Reaction equation

HRID 483574 reaction equation
[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](Cl)=[O:24])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].N1C=CC=CC=1.[CH3:32][C:33]1[N:34]([C:38]2[CH:43]=[CH:42][C:41]([NH2:44])=[CH:40][CH:39]=2)[CH:35]=[CH:36][N:37]=1>O1CCCC1>[CH3:32][C:33]1[N:34]([C:38]2[CH:43]=[CH:42][C:41]([NH:44][C:23](=[O:24])[CH2:22][C:19]3[CH:20]=[CH:21][C:16]([O:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:17][CH:18]=3)=[CH:40][CH:39]=2)[CH:35]=[CH:36][N:37]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31574784-(2-methyl-1H-imidazol-1-yl)anilineHCID 10021844p-Tetradecyloxyphenylacetylchloride

Product 1

HCID 15030162N-[4-(2-methyl-1H-imidazol-1-yl)phenyl]-4-(tetradecyloxy)benzeneacetamideYield 58.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5.0 g of p-tetradecyloxy phenylacetyl chloride in 50 ml of tetrahydrofuran is added to a solution of 4.31 g of pyridine and 2.36 g of 4-(2-methyl-1H-imidazol-1-yl)benzenamine in 50 ml of tetrahydrofuran over 5 minutes. The mixture is stirred at ambient temperature for 1 hour, heated to reflux and allowed to stir at room temperature for 2 hours. The solvent is evaporated to a residue which is partitioned between chloroform and dilute sodium bicarbonate. The organic layer is separated, washed with water, dried and filtered through a pad of magnesium silicate. The solvent is evaporated to an oil which crystallizes from methyl alcohol:water to give 4.0 g of white solid Which is chromatographed on silica gel using ethyl acetate containing 0.1% ammonium hydroxide to give 3.9 g of the desired product as a white solid, m.p. 106°-109° C.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. stirringto stir at room temperature for 2 hours
  4. customThe solvent is evaporated to a residue which
  5. customis partitioned between chloroform and dilute sodium bicarbonate
  6. customThe organic layer is separated
  7. washwashed with water
  8. customdried
  9. filtrationfiltered through a pad of magnesium silicate
  10. customThe solvent is evaporated to an oil which
  11. customcrystallizes from methyl alcohol

Sources & evidence

ORD record
ord-ea21e8825c33429fa7ccfbd8f74d2288
Source dataset
uspto-grants-1993_07
Patent number
US05225425

Reaction notes

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