Methanol → HCID 13603719, compound

HRID 651909Notes

Reaction equation

HRID 651909 reaction equation
S(Cl)(Cl)=O.[C:5]([C:8]1[CH:9]=[C:10]([C:14]2[C:15](=[O:26])[C:16]([N:21]3[CH:25]=[CH:24][CH:23]=[N:22]3)=[CH:17][N:18]([CH3:20])[CH:19]=2)[CH:11]=[CH:12][CH:13]=1)([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:32]O>>[CH3:32][O:6][C:5]([C:8]1[CH:9]=[C:10]([C:14]2[C:15](=[O:26])[C:16]([N:21]3[CH:25]=[CH:24][CH:23]=[N:22]3)=[CH:17][N:18]([CH3:20])[CH:19]=2)[CH:11]=[CH:12][CH:13]=1)=[O:7]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 20198099HCID 20198099, compound

Product 1

HCID 13603719HCID 13603719, compoundYield 91%

Procedure

24 ml (0.33 mole) of thionyl chloride are added dropwise to 30 g (0.09 mole) of 5-(3-carboxyphenyl)-1-methyl-3-(pyrazol-1-yl)-4-pyridone-sulphuric acid adduct in 100 ml of methanol at 0° C. to 10° C.; when the addition has ended, the mixture is stirred at room temperature for 12 hours and concentrated in vacuo, the oil which remains is taken up in 100 ml of water and the mixture is rendered weakly alkaline with aqueous sodium carbonate solution and extracted three times with 100 ml of methylene chloride each time. The combined organic phases are washed with water, dried over sodium sulphate and concentrated in vacuo. The crystals which remain are digested with ether, filtered off with suction and dried. 20 g (91% of theory) of 5-(3-methoxycarbonylphenyl)-1-methyl-3-(pyrazol-1-yl)-4-pyridone of melting point 144° C. are obtained.

Workup

  1. additionwhen the addition
  2. concentrationconcentrated in vacuo
  3. extractionextracted three times with 100 ml of methylene chloride each time
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. filtrationfiltered off with suction
  8. customdried

Sources & evidence

ORD record
ord-361d39b2883844138e139d3b304ec694
Source dataset
uspto-grants-1987_06
Patent number
US04670044

Reaction notes

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