Sulfuric Acid → HCID 19841371, compound

HRID 1638595Notes

Reaction equation

HRID 1638595 reaction equation
N[C:2]1[CH:3]=[C:4]2[NH:10][C:9]([S:11][CH2:12][C:13]3[C:18]([CH3:19])=[C:17]([O:20][CH3:21])[C:16]([CH3:22])=[CH:15][N:14]=3)=[N:8][C:5]2=[N:6][CH:7]=1.S(=O)(=O)(O)[OH:24].N([O-])=O.[Na+].[OH-].[Na+]>O>[OH:24][C:2]1[CH:3]=[C:4]2[NH:10][C:9]([S:11][CH2:12][C:13]3[C:18]([CH3:19])=[C:17]([O:20][CH3:21])[C:16]([CH3:22])=[CH:15][N:14]=3)=[N:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 13768261HCID 13768261, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 19841371HCID 19841371, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

0.2 Gram of 6-amino-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methylthio]imidazo[4,5-b]pyridine was dissolved in a mixture consisting of 3 ml of water and 0.1 ml of concentrated sulfuric acid. This mixture was stirred at 0° C., and 59 mg of sodium nitrite was added, then the mixture was further stirred at the same temperature for 1 hour. The reaction solution was neutralized by adding 4N-sodium hydroxide aqueous solution, and the crystals formed were collected by filtration. Recrystallized from ethanol to obtain 0.2 g of 6-hydroxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methylthio]imidazo[4,5-b]pyridine in the form of yellow powdery crystals. Melting point: 178°-179.5° C.

Workup

  1. stirringthe mixture was further stirred at the same temperature for 1 hour
  2. customthe crystals formed
  3. filtrationwere collected by filtration
  4. customRecrystallized from ethanol

Sources & evidence

ORD record
ord-acf4607c25dc42e0881b122329d7517a
Source dataset
uspto-grants-1989_11
Patent number
US04880815

Reaction notes

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