Acetic Acid → 4-[4-[3-(1-Imidazolyl)propyl]phenoxymethyl]-2-(4-methyl-2-thienyl)oxazole

HRID 322452Notes

Reaction equation

HRID 322452 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[O:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][N:23]4[CH:27]=[CH:26][N:25]=[CH:24]4)=[CH:16][CH:15]=3)[N:11]=2)=[CH:4][C:3]=1[CH3:28].C(O)(=O)C>[Zn].O>[N:23]1([CH2:22][CH2:21][CH2:20][C:17]2[CH:16]=[CH:15][C:14]([O:13][CH2:12][C:10]3[N:11]=[C:7]([C:5]4[S:6][CH:2]=[C:3]([CH3:28])[CH:4]=4)[O:8][CH:9]=3)=[CH:19][CH:18]=2)[CH:27]=[CH:26][N:25]=[CH:24]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 220095972-(5-Bromo-4-methyl-2-thienyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazole

Product 1

HCID 220098524-[4-[3-(1-Imidazolyl)propyl]phenoxymethyl]-2-(4-methyl-2-thienyl)oxazoleYield 81.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-(5-bromo-4-methyl-2-thienyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazole (700 mg), zinc powder (200 mg), acetic acid (5 ml) and water (5 ml) was heated for 4 hours under reflux. The residue was filtered off, the filtrate was concentrated. To the residue was added ethyl acetate, washed with saturated aqueous sodium bicarbonate and water, dried (MgSO4), and concentrated under reduced pressure to give crystals of 4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-(4-methyl-2-thienyl)oxazole (470 mg, 81%). Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 077-178° C.

Workup

  1. temperaturewas heated for 4 hours
  2. temperatureunder reflux
  3. filtrationThe residue was filtered off
  4. concentrationthe filtrate was concentrated
  5. additionTo the residue was added ethyl acetate
  6. washwashed with saturated aqueous sodium bicarbonate and water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8a52b826359f4694a8ab2506c7fb5798
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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