Acetic Acid → HCID 22151440, compound

HRID 703186Notes

Reaction equation

HRID 703186 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.C[O-].[Na+].[C:28](O)(=[O:30])C>CO>[CH3:28][O:30][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 176Acetic AcidHCID 10942334Sodium MethoxideHCID 22151448HCID 22151448, compound

Product 1

HCID 22151440HCID 22151440, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 500 mg of 6-[[(3-methyl-4-nitro-2-pyridyl)methyl]thio]-5H-1,3-dioxolo[4,5-f]benzimidazole in 20 ml of absolute methanol was treated with 300 mg of sodium methylate, whereupon the mixture was boiled at reflux under argon for 18 hours. The reaction mixture was buffered by means of glacial acetic acid and concentrated in vacuo. The residue was treated with methylene chloride/sodium bicarbonate solution, whereupon the organic solution was dried and concentrated. By recrystallization from ethyl acetate there was obtained 6-[[(4-methoxy-3-methyl-2-pyridyl)methyl]thio]-5H-1,3-dioxolo[45-f]benzimidazole of melting point 215°-220°.

Workup

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

Sources & evidence

ORD record
ord-1ea167d59cd348cd9ea0c505f16f0835
Source dataset
uspto-grants-1991_01
Patent number
US04981861

Reaction notes

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