Methane → HCID 18465367, compound

HRID 437537

Reaction equation

HRID 437537 reaction equation
[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[NH:11][CH:10]=[N:9][C:8]=2[N:7]([CH2:15][CH2:16][CH3:17])[C:5]1=[O:6])[CH2:2][CH3:3].[OH-].[Na+].Cl[CH2:21][CH:22]([OH:25])[CH2:23][OH:24].C>O.C(O)(C)C.C(Cl)(Cl)Cl.CO>[OH:25][CH:22]([CH2:23][OH:24])[CH2:21][N:11]1[C:12]2[C:13](=[O:14])[N:4]([CH2:1][CH2:2][CH3:3])[C:5](=[O:6])[N:7]([CH2:15][CH2:16][CH3:17])[C:8]=2[N:9]=[CH:10]1

Participants

8

Reactant 4

HCID 297MethaneHCID 72903-Chloro-1,2-propanediolHCID 14798Sodium HydroxideHCID 1693171,3-Dipropylxanthine

Product 1

HCID 18465367HCID 18465367, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolvent2×HCID 21584188Chloroform methanolSolvent

Procedure

A suspension of 1,3-di-n-propylxanthine (250.1 g., 1.06 mole) in water (300 ml.) was treated with sodium hydroxide solution (50%, 85 ml.). The mixture was filtered, and evaporated to dryness. The residue obtained was treated with a solution of 1-chloro-2,3-dihydroxypropane (170 g., 1.59 mole) in isopropanol (700 ml.). The mixture was stirred at reflux overnight, filtered, and evaporated to dryness to obtain a brown gummy residue. This residue was dissolved in isopropyl alcohol, and stirred overnight with charcoal (20 gm.). The mixture was filtered, concentrated and allowed to crystallize over night at 0° to -5° C. The crystals were filtered, suspended in ether, refiltered and air dried to yield white crystals (224 g., 72.17%), melting point 88° - 91°. Tlc (5μl of a 5% solution) on a silica plate developed in chloroform:methanol (9.5:0.5) showed one spot. IR and NMR spectra were consistent with the proposed structure.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated to dryness
  3. customThe residue obtained
  4. temperatureat reflux overnight
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customto obtain a brown gummy residue
  8. filtrationThe mixture was filtered
  9. concentrationconcentrated
  10. customto crystallize over night at 0° to -5° C
  11. filtrationThe crystals were filtered
  12. customair dried
  13. customto yield white crystals (224 g., 72.17%), melting point 88° - 91°

Sources & evidence

ORD record
ord-416bfc39d5184c4ca3f8be7fd02d440f
Source dataset
uspto-grants-1977_06
Patent number
US04031218

Linked notes

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