Thionyl Chloride → HCID 178463031, compound

HRID 1076553Notes

Reaction equation

HRID 1076553 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([OH:15])=[C:10]([C:12](O)=[O:13])[N:11]=[C:6]2[CH:5]=[N:4]1)[CH3:2].S(Cl)([Cl:18])=O>>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([OH:15])=[C:10]([C:12]([Cl:18])=[O:13])[N:11]=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 178463032HCID 178463032, compound

Product 1

HCID 178463031HCID 178463031, compound

Procedure

31.3 g. of 1-ethyl-6-hydroxy-1H-pyrazolo[3,4-b]-pyrazine-5-carboxylic acid (0.15 mol.) are carefully added in portions to 300 ml. of thionyl chloride. As soon as the gas evolution has ceased, the mixture is heated at reflux for 3 hours. After removal of excess thionyl chloride under vacuum, the residue is dissolved in benzene. Evaporation of the benzene provides 30.5 g. (90%) of amorphous 1-ethyl-6-hydroxy-1H-pyrazolo[3,4-b]pyrazine-5-carbonyl chloride which is used without further purification.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 3 hours
  3. customAfter removal of excess thionyl chloride under vacuum
  4. dissolutionthe residue is dissolved in benzene
  5. customEvaporation of the benzene
  6. customprovides 30.5 g
  7. custom(90%) of amorphous 1-ethyl-6-hydroxy-1H-pyrazolo[3,4-b]pyrazine-5-carbonyl chloride which is used without further purification

Sources & evidence

ORD record
ord-176c8a9caffd41e88baba9977a722baf
Source dataset
uspto-grants-1976_05
Patent number
US03957782

Reaction notes

Loading…