Ethyl orthopropionate → HCID 21254783, compound

HRID 636482Notes

Reaction equation

HRID 636482 reaction equation
[NH2:1][C:2]1[C:8]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:19](OCC)(OCC)(OCC)[CH2:20][CH3:21]>C(O)(=O)C>[CH2:20]([C:21]1[NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[C:8]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[C:2]=2[N:1]=1)[CH3:19]

Participants

4

Reactant 2

HCID 66995Ethyl orthopropionateHCID 21254704HCID 21254704, compound

Product 1

HCID 21254783HCID 21254783, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 2-amino-3-(4-methoxybenzyloxy)-aniline (1.15 g) in acetic acid (12 ml) was added triethyl orthopropionate (994 mg) at ambient temperature, and the mixture was stirred overnight. The reaction mixture was concentrated in vacuo, and the residue was extracted with dichloromethane. The organic layer was washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo to give 2-ethyl-4-(4-methoxybenzyloxy)-1H-benzimidazole (900 mg) as pale yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionthe residue was extracted with dichloromethane
  3. washThe organic layer was washed with saturated sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-b05f6d0de7514da9a35e5c81465f1785
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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