Toluene → Chinoin 170

HRID 1285161Notes

Reaction equation

HRID 1285161 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].C[O-].[Na+].[C:22]1(C)C=CC=C[CH:23]=1>C(OCC)(=O)C>[CH3:22][C:23]1[O:18][N:17]=[C:15]([CH2:14][N:10]2[C:11]3[C:12](=[O:13])[N:1]([CH3:2])[C:3](=[O:4])[N:5]([CH3:6])[C:7]=3[N:8]=[CH:9]2)[N:16]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 30574902-(Theophyllin-7-yl)-acetamidoximeHCID 10942334Sodium Methoxide

Product 1

HCID 139570Chinoin 170Yield 74%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

5.04 g. 2-(theophyllin-7-yl)-acetamidoxime, 2.16 g. of sodium methylate, 10 cm3 ethyl acetate and 200 cm3 of toluene are heated under stirring by using a water condenser for 20 hours and further 10 cm3 ethyl acetate are added to the mixture in five portions. The solvent is distilled off. After crystallization from water 4.1 g. (74% yield) 7-[(5-methyl-1,2,4-oxadiazol-3-yl)-methyl]-theophylline are obtained. M.p.: 135°-136° C.

Workup

  1. customfor 20 hours
  2. distillationThe solvent is distilled off
  3. customAfter crystallization from water 4.1 g

Sources & evidence

ORD record
ord-3b98f4533d1747679f1234a3e24d5c28
Source dataset
uspto-grants-1986_01
Patent number
US04565817

Reaction notes

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