Ethylene Glycol → HCID 22163737, compound

HRID 1087726Notes

Reaction equation

HRID 1087726 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][CH:12]=[O:13])[C:6]=2[C:5](=[O:14])[NH:4][C:3]1=[O:15].N1([C:27](=[O:28])[C:26]2N(CC=O)C=NC=2N(C)C1=O)C.C(O)CO.C1(C)C=CC=CC=1>O>[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][CH:12]3[O:28][CH2:27][CH2:26][O:13]3)[C:6]=2[C:5](=[O:14])[NH:4][C:3]1=[O:15]

Participants

6

Reactant 4

HCID 174Ethylene Glycol2×HCID 1140TolueneHCID 14482471(1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)acetaldehydeHCID 22163746HCID 22163746, compound

Product 1

HCID 22163737HCID 22163737, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20.8 g 2-(3-methyl-xanthine-7-yl)-acetaldehyde (Formula IV)-prepared similarly like 7-theophyllinyl acetaldehyde Il Farmaco, Ed. Sc. 17, 73; (1962), 40.0 ethylene glycol (Formula II) 2.5 g DOWEX 50 W synthetic resin and 1,000.0 cm3 toluene are heated under stirring in a flask equipped with a water condenser and a cooler until water condensation ceases. The reaction mixture is filtered hot and the precipitate is washed with hot toluene and the filtrate is washed upon cooling with 5% sodium hydrogen carbonate and the organic layer is evaporated after drying. The residue is crystallized three times from propanol and 2-[(3-methyl-xanthine-7-yl)methyl]-1,3-dioxolane is obtained with a yield of 55%, melting point 276°-278° C.

Workup

  1. temperatureare heated
  2. customequipped with a water condenser
  3. filtrationThe reaction mixture is filtered hot
  4. washthe precipitate is washed with hot toluene
  5. washthe filtrate is washed
  6. temperatureupon cooling with 5% sodium hydrogen carbonate
  7. customthe organic layer is evaporated
  8. customafter drying
  9. customThe residue is crystallized three times from propanol

Sources & evidence

ORD record
ord-1de6314232d54ea3845a79fcd919390e
Source dataset
uspto-grants-1990_10
Patent number
US04960773

Reaction notes

Loading…