Methanol → HCID 22151440, compound

HRID 35463Notes

Reaction equation

HRID 35463 reaction equation
[CH3:1][C:2]1[C:3]([CH2:11][S:12][C:13]2[NH:14][C:15]3[CH:21]=[C:20]4[O:22][CH2:23][O:24][C:19]4=[CH:18][C:16]=3[N:17]=2)=[N:4][CH:5]=[CH:6][C:7]=1[N+]([O-])=O.[CH3:25][OH:26].C[O-].[Na+]>C(O)(=O)C>[CH3:25][O:26][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([CH2:11][S:12][C:13]2[NH:14][C:15]3[CH:21]=[C:20]4[O:22][CH2:23][O:24][C:19]4=[CH:18][C:16]=3[N:17]=2)[C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 22151448HCID 22151448, compound

Product 1

HCID 22151440HCID 22151440, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 500 mg (1.45 mmol) of 6-[[(3-methyl-4-nitro-2-pyridyl)methyl]thio]-5H-1,3-dioxolo[4,5-f]-benzimidazole in 20 ml of abs. methanol is treated with 300 mg of sodium methylate, whereupon the mixture is boiled at reflux under argon for 18 hours. The reaction mixture is buffered by means of glacial acetic acid and concentrated in vacuo. The residue is treated with methylene chloride/sodium bicarbonate solution, whereupon the organic solution is dried and concentrated. By recrystallization from ethyl acetate there is obtained 6-[[(4-methoxy-3-methyl-2-pyridyl)methyl)thio)-5H-1,3-dioxolo[4,5-f]benzimidazole of melting point 215°-220°.

Workup

  1. temperatureat reflux under argon for 18 hours
  2. concentrationconcentrated in vacuo
  3. additionThe residue is treated with methylene chloride/sodium bicarbonate solution, whereupon the organic solution
  4. customis dried
  5. concentrationconcentrated
  6. customBy recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-b7c5adcb5e024efda99980a2d569d9a3
Source dataset
uspto-grants-1988_08
Patent number
US04766133

Reaction notes

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