Methane → HCID 86740607, compound

HRID 1285179Notes

Reaction equation

HRID 1285179 reaction equation
[N:1]1([C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15](=[N:17][OH:18])[NH2:16])[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].[CH3:19][O-].[Na+].[N:22]1([C:33](=[O:34])[C:32]2[N:31]([CH2:35]C(Cl)=O)[CH:30]=[N:29][C:28]=2[N:26]([CH3:27])[C:24]1=[O:25])[CH3:23].C>CN(C)C=O>[N:1]1([C:12](=[O:13])[C:11]2[N:10]([CH2:14][CH:15]3[N:16]=[C:35]([N:31]4[C:32]5[C:33](=[O:34])[N:22]([CH3:23])[C:24](=[O:25])[N:26]([CH3:27])[C:28]=5[N:29]=[CH:30]4)[O:18][N:17]3[CH3:19])[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2]

Participants

6

Reactant 4

HCID 297MethaneHCID 30161851,2,3,6-Tetrahydro-1,3-dimethyl-2,6-dioxo-7H-purine-7-acetyl chlorideHCID 30574902-(Theophyllin-7-yl)-acetamidoximeHCID 10942334Sodium Methoxide

Product 1

HCID 86740607HCID 86740607, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5.04 g. of 2-(theophyllin-7-yl)-acetamidoxime and 1.08 g. of sodium methylate are suspended in 60 cm3 dimethylformamide whereafter a solution of 5.13 g. of theophyllin-7-yl-acetyl chloride in 25 cm3 of dimethyl-formamide is added dropwise within 15 minutes. The mixture is heated for 1 hour and after adding a small amount of activated charcoal it is filtered while hot and the filtrate is evaporated at reduced pressure. The residue is dissolved in 100 cm3 0.1N sodium hydrogen carbonate solution while hot and after cooling the crystals are filtered by suction, washed with water and crystallized from 50% aqueous ethanol. Thus 6.6 g. of 3-(theophyllin-7-yl-methyl)-5-(theophylline-7-yl)-methyl-1,2,4-oxadiazole are obtained, m.p.: 271°-272° C.

Workup

  1. temperatureThe mixture is heated for 1 hour
  2. filtrationis filtered while hot and the filtrate
  3. customis evaporated at reduced pressure
  4. dissolutionThe residue is dissolved in 100 cm3 0.1N sodium hydrogen carbonate solution while hot and
  5. temperatureafter cooling the crystals
  6. filtrationare filtered by suction
  7. washwashed with water
  8. customcrystallized from 50% aqueous ethanol

Sources & evidence

ORD record
ord-5d06331c63064c7a8648c89ff3742de7
Source dataset
uspto-grants-1986_01
Patent number
US04565817

Reaction notes

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