Sulfur Dioxide → HCID 14129246, compound

HRID 1762038Notes

Reaction equation

HRID 1762038 reaction equation
N[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:5]=[N:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].N([O-])=O.[Na+].C(Cl)(Cl)[Cl:23].S(=O)=O>Cl.O>[Cl:23][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:5]=[N:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

7

Reactant 4

HCID 1119Sulfur DioxideHCID 6212ChloroformHCID 14129245HCID 14129245, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 14129246HCID 14129246, compoundYield 550.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

11.0 g of 5-amino-4-ethoxycarbonyl-1-(2-pyridyl)imidazole was dissolved in 60 ml of conc. hydrochloric acid and the resulting solution was cooled to -5° C. Subsequently, 3.9 g of sodium nitrite was dissolved in 10 ml of water and the resulting solution was added dropwise to the previously prepared solution while maintaining the temperature at -5° C. or lower. After completion of the dropwise addition, the resulting mixture was stirred at the same temperature for 0.5 hour. The thus obtained solution was added dropwise at around 5° C. to 150 ml of a solution of chloroform containing 1.0 g of cuprous chloride and 12 g of sulfur dioxide. After the resulting mixture was stirred at room temperature for 1 hour, was added thereto 300 ml of water and the organic layer was separated. The aqueous layer was extracted with chloroform and the organic layers were combined, washed with water and dried. The solvent was then removed by distillation to give 11.6 g of 5-chloro-4-ethoxycarbonyl-1-(2-pyridyl)imidazole as an oil.

Workup

  1. additionthe resulting solution was added dropwise to the previously prepared solution
  2. temperaturewhile maintaining the temperature at -5° C.
  3. additionAfter completion of the dropwise addition
  4. stirringAfter the resulting mixture was stirred at room temperature for 1 hour
  5. additionwas added
  6. custom300 ml of water and the organic layer was separated
  7. extractionThe aqueous layer was extracted with chloroform
  8. washwashed with water
  9. customdried
  10. customThe solvent was then removed by distillation

Sources & evidence

ORD record
ord-06677881171f4b0da64be84436eb38f4
Source dataset
uspto-grants-1989_05
Patent number
US04830660

Reaction notes

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