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

HRID 636485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 636485
[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 solution of 2-amino-3-benzyloxy-N-methylaniline (318.5 mg) in acetic acid (3.2 ml) was added tetramethyl orthocarbonate (233 pl) 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 (27.3 mg).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ca4eab4bafa541feaf67ead0c9ee0505
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194396B1

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