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

HRID 613600Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 613600
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d7d1ba524b8c4248ad6b1cfa84899827
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06008229

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