Tetramethyl orthocarbonate → 4-benzyloxy-2-methoxy-1-methyl-1H-benzimidazole

HRID 1871100Notes

Reaction equation

HRID 1871100 reaction equation
[NH2:1][C:2]1[C:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=[CH:6][C:3]=1[NH:4][CH3:5].[C:18]([O:25][CH3:26])(OC)(OC)OC>C(O)(=O)C>[CH2:11]([O:10][C:9]1[C:2]2[N:1]=[C:18]([O:25][CH3:26])[N:4]([CH3:5])[C:3]=2[CH:6]=[CH:7][CH:8]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 74613Tetramethyl orthocarbonateHCID 104895412-amino-3-benzyloxy-N-methylaniline

Product 1

HCID 107543614-benzyloxy-2-methoxy-1-methyl-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 2-amino-3-benzyloxy-N-methylaniline (318.5 mg) in acetic acid (3.2 ml) was added tetramethyl orthocarbonate (223.0 μl) at ambient temperature, and the reaction mixture was stirred for 4 hours. The reaction mixture was concentrated in vacuo, and to the residue were added ethyl acetate and a saturated sodium bicarbonate solution. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was triturated with n-hexane-diisopropyl ether to give 4-benzyloxy-2-methoxy-1-methyl-1H-benzimidazole (273.3 mg) as a pale brown solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionto the residue were added ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with n-hexane-diisopropyl ether

Sources & evidence

ORD record
ord-d0ecd894acb74a538546d69f0a9fe56c
Source dataset
uspto-grants-2000_08
Patent number
US06100284

Reaction notes

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