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

HRID 2287562Notes

Reaction equation

HRID 2287562 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 solution of 2-amino-3-benzyloxy-N-methylaniline (318.5 mg) in acetic acid (3.2 ml) was added tetramethyl orthocarbonate (233 μl) at ambient temperature, and the mixture was stirred for 4 hours. The reaction mixture was concentrated in vacuo, and to the residue were added ethyl acetate and saturated sodium bicarbonate solution. The separated organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was removed in vacuo to give 4-benzyloxy-2-methoxy-1-methyl-1H-benzimidazole (273.3 mg).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionto the residue were added ethyl acetate and saturated sodium bicarbonate solution
  3. washThe separated organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-9d12918a6ec14beb95496c65b3471982
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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