Dimethyl Sulfoxide → HCID 12774893, compound

HRID 848637Notes

Reaction equation

HRID 848637 reaction equation
Cl[CH:2]1[CH2:6][CH2:5][O:4][CH:3]1[N:7]1[C:12](=[O:13])[NH:11][C:10](=[O:14])[CH:9]=[N:8]1.CC(C)([O-])C.[K+].CS(C)=O>C(O)(=O)C>[O:4]1[CH2:5][CH:6]=[CH:2][CH:3]1[N:7]1[C:12](=[O:13])[NH:11][C:10](=[O:14])[CH:9]=[N:8]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 127749012-(3-Chlorooxolan-2-yl)-1,2,4-triazine-3,5(2H,4H)-dioneHCID 23665647Potassium tert-butoxide

Product 1

HCID 12774893HCID 12774893, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-(3-Chloro-tetrahydro-2-furanyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine (0.8 g) and potassium t-butoxide (0.7 g) are added to dimethyl sulfoxide (3 ml), and the mixture is stirred at room temperature for 3 hours. The reaction mixture is poured into ice-water. The mixture is acidified with acetic acid and extracted with chloroform. The chloroform extract is washed with water, dried and evaporated to remove the solvent. The crude residue is recrystallized from ethanol to give 2-(2,5-dihydro-2-furanyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine (Compound No. 81). Yield, 0.5 g (76%). M.P., 147°-148° C.

Workup

  1. extractionextracted with chloroform
  2. extractionThe chloroform extract
  3. washis washed with water
  4. customdried
  5. customevaporated
  6. customto remove the solvent
  7. customThe crude residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-aed1f257c4e94e90b2af6397342a3b5f
Source dataset
uspto-grants-1981_10
Patent number
US04297129

Reaction notes

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