Hydrochloric Acid → 2-Ethylamino-6-[2-(2-imidazolyl)ethyl]benzoxazole

HRID 728171

Reaction equation

HRID 728171 reaction equation
C([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH:13]=[CH:14][C:15]1[CH:26]=[CH:25][C:18]2[N:19]=[C:20]([NH:22][CH2:23][CH3:24])[O:21][C:17]=2[CH:16]=1)C1C=CC=CC=1.Cl>[Pd].CO>[CH2:23]([NH:22][C:20]1[O:21][C:17]2[CH:16]=[C:15]([CH2:14][CH2:13][C:9]3[NH:8][CH:12]=[CH:11][N:10]=3)[CH:26]=[CH:25][C:18]=2[N:19]=1)[CH3:24]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 543240066-[2-(1-Benzylimidazol-2-yl)vinyl]-2-ethylaminobenzoxazole

Product 1

HCID 151715482-Ethylamino-6-[2-(2-imidazolyl)ethyl]benzoxazoleYield 19.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (0.5 g) was added to a mixture of 6-[2-[1-benzylimidazol-2-yl)vinyl]-2-ethylaminobenzoxazole (0.9 g) in a solution of methanol (50 ml) and conc. hydrochloric acid (6 ml), and the mixture was subjected to catalytic reduction under atmospheric pressure for 6 hours at ambient temperature. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. The residue was purified by a column chromatography on alumina and eluted with a chloroform. The eluted fractions containing the desired product were collected and evaporated in vacuo. The residue was triturated with diethyl ether to give 2-ethylamino-6-[2-(2-imidazolyl)ethyl]benzoxazole (0.13 g).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by a column chromatography on alumina
  4. washeluted with a chloroform
  5. additionThe eluted fractions containing the desired product
  6. customwere collected
  7. customevaporated in vacuo
  8. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-1578c1e68d4c4e189324d71981d7322a
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Linked notes

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