Glyoxal → Lcb-2183

HRID 326874Notes

Reaction equation

HRID 326874 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[NH2:9][C:10]1[N:15]=[C:14]([CH2:16][O:17][CH2:18][CH3:19])[NH:13][C:12](=[O:20])[C:11]=1[N:21]=O.[CH:23]([CH:25]=O)=O>O>[CH2:18]([O:17][CH2:16][C:14]1[NH:13][C:12](=[O:20])[C:11]2[C:10](=[N:9][CH:23]=[CH:25][N:21]=2)[N:15]=1)[CH3:19]

Participants

5

Reactant 3

HCID 7860GlyoxalHCID 24489Sodium DithioniteHCID 1354111536-Amino-2-(ethoxymethyl)-5-nitroso-4(3H)-pyrimidinone

Product 1

HCID 135418284Lcb-2183

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 19.1 g (0.11 mole) of sodium dithionite in 88 ml of water is added dropwise to a suspension, maintained at 20° C., of 10.0 g (0.050 mole) of 6-amino-2-(ethoxymethyl)-5-nitroso-4(3H)-pyrimidinone in 50 ml of water. After being stirred for 30 minutes at room temperature, the reaction mixture, still maintained at 20° C., is treated with 47.9 g (0.33 mole) of a 40% aqueous solution of glyoxal. Stirring is continued for 20 hours at room temperature. The solution obtained is then extracted with dichloromethane. These organic extracts are dried over sodium sulphate and concentrated to dryness under reduced pressure. The solid residue is recrystallized from methanol in the presence of Norit. Yld: 6.5 g (63%), m.p. 168°-169° C. The product is identical to that obtained in Example 1.

Workup

  1. temperaturethe reaction mixture, still maintained at 20° C.
  2. stirringStirring
  3. waitis continued for 20 hours at room temperature
  4. customThe solution obtained
  5. extractionis then extracted with dichloromethane
  6. dry with materialThese organic extracts are dried over sodium sulphate
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe solid residue is recrystallized from methanol in the presence of Norit
  9. customthat obtained in Example 1

Sources & evidence

ORD record
ord-cc098ef4715a4ff8bbcafd4c1e74e798
Source dataset
uspto-grants-1993_12
Patent number
US05270465

Reaction notes

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