Glyoxal → HCID 178463125, compound

HRID 399944Notes

Reaction equation

HRID 399944 reaction equation
[CH2:1]([N:3]1[C:7]([OH:8])=[C:6]([C:9](=[O:25])[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:12]([NH:20][CH2:21][CH2:22][OH:23])[C:11]=2[Cl:24])[CH:5]=[N:4]1)[CH3:2].[CH:26]([CH:28]=[O:29])=O>C1(C)C=CC=CC=1>[CH2:1]([N:3]1[C:7]([OH:8])=[C:6]([C:9](=[O:25])[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:17])=[O:18])=[C:12]([N:20]3[CH2:26][CH2:28][O:29][C:22](=[O:23])[CH2:21]3)[C:11]=2[Cl:24])[CH:5]=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 7860Glyoxal2×HCID 178463131HCID 178463131, compound

Product 1

HCID 178463125HCID 178463125, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 0.50 g (1.3 mmol) of 1-ethyl-4-(2-chloro-3-(2-hydroxyethylamino)-4-methylsulfonylbenzoyl)-5-hydroxypyrazole in 20 mL of toluene was heated to 90° C. and treated with 2 mL of 40 percent aqueous glyoxal solution with stirring. The progress of the reaction was monitored by HPLC analysis and additional aliquots of 40 percent aqueous glyoxal solution were added every few hours until the starting material was consumed. After 24 hours, the reaction was complete and the dark solution was decanted from a gummy residue. The residue was extracted with several portions of hot toluene and the organic solutions were combined. The volatiles were removed by evaporation under reduced pressure and the resulting residue was purified by adding a small amount of diethyl ether and collecting the solids present by filtration. More solids were obtained when the diethyl ether solution was concentrated by evaporation. These solids were collected by filtration as well. The solids were combined to obtain 0.39 g (71 percent of theory) of the title compound as a tan powder melting at 198°-202° C.

Workup

  1. additionwere added every few hours until the starting material
  2. customwas consumed
  3. customthe dark solution was decanted from a gummy residue
  4. extractionThe residue was extracted with several portions of hot toluene
  5. customThe volatiles were removed by evaporation under reduced pressure
  6. customthe resulting residue was purified
  7. additionby adding a small amount of diethyl ether
  8. customcollecting the solids
  9. filtrationpresent by filtration
  10. customMore solids were obtained when the diethyl ether solution
  11. concentrationwas concentrated by evaporation
  12. filtrationThese solids were collected by filtration as well

Sources & evidence

ORD record
ord-10010eacd42741db9a7e3e5708a05cfe
Source dataset
uspto-grants-1998_10
Patent number
US05824802

Reaction notes

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