Glyoxal → HCID 12918841, compound

HRID 1155479Notes

Reaction equation

HRID 1155479 reaction equation
[CH3:1][C:2]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([NH:13][CH3:14])=[O:12])[CH:6]=1)([CH3:4])[CH3:3].[CH:15]([CH:17]=[O:18])=[O:16].[OH-].[Na+]>C(O)C>[CH3:4][C:2]([C:5]1[O:9][N:8]=[C:7]([N:10]2[CH:15]([OH:16])[CH:17]([OH:18])[N:13]([CH3:14])[C:11]2=[O:12])[CH:6]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 7860GlyoxalHCID 14798Sodium HydroxideHCID 186687Monoisouron

Product 1

HCID 12918841HCID 12918841, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2.0 grams (0.010 mole) of 1-[5-(1,1-dimethylethyl)-3-isoxazolyl]-3-methylurea in 50 milliliters of 95 percent ethanol was added 7.3 grams of a 40 percent aqueous glyoxal solution which had been previously adjusted to pH 7 with dilute sodium hydroxide solution. After standing at room temperature overnight, the solution was topped on a rotary evaporator to give an oily residue which was extracted with two 20 milliliter portions of chloroform. The extract was washed with saturated sodium chloride solution, filtered through silicone-treated paper, and concentrated on a rotary evaporator to give 2.0 grams of oily residue. Crystallization from ether gave 0.4 grams of white crystals of 3-[5-(1,1-dimethylethyl)-3-isoxazolyl]-4,5-dihydroxy-1-methyl-2-imidazolidinone, M.P. 153°-157° C., which had consistent mass, infrared and NMR spectra.

Workup

  1. customthe solution was topped on a rotary evaporator
  2. customto give an oily residue which
  3. extractionwas extracted with two 20 milliliter portions of chloroform
  4. washThe extract was washed with saturated sodium chloride solution
  5. filtrationfiltered through silicone-
  6. additiontreated paper
  7. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-226a0840e564419e92ffa3aaab41cb7d
Source dataset
uspto-grants-1981_11
Patent number
US04302239

Reaction notes

Loading…