Acetone → HCID 86737831, compound

HRID 1156621Notes

Reaction equation

HRID 1156621 reaction equation
[NH2:1][C:2]1[N:7]2[O:8][C:9](=[O:11])[N:10]=[C:6]2[N:5]=[C:4]([N:12]([CH2:16][CH:17]=[CH2:18])[CH2:13][CH:14]=[CH2:15])[N:3]=1.Cl[CH2:20][C:21]([O:23][CH3:24])=[O:22].[C:25](=O)([O-])[O-:26].[K+].[K+].C[C:32]([CH3:34])=[O:33]>>[CH2:13]([N:12]([CH2:16][CH:17]=[CH2:18])[C:4]1[N:3]=[C:2]([N:1]([CH2:34][C:32]([O:26][CH3:25])=[O:33])[CH2:20][C:21]([O:23][CH3:24])=[O:22])[N:7]2[O:8][C:9](=[O:11])[N:10]=[C:6]2[N:5]=1)[CH:14]=[CH2:15]

Participants

5

Reactant 4

HCID 180AcetoneHCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 20535125HCID 20535125, compound

Product 1

HCID 86737831HCID 86737831, compound

Procedure

3.0 g. of 7-amino-5-diallylamino-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-2-one are dissolved in 120 ml. of acetone and treated with 6 ml. of methyl chloroacetate and 15 g. of potassium carbonate. The mixture is stirred for 52 hours and then evaporated to dryness. The residue is dissolved in methylene chloride and water and then extracted twice with methylene chloride. The combined organic extracts are dried over potassium carbonate and evaporated under reduced pressure. The residue is chromatographed over silica gel using a 0.5% mixture of methanol in methylene chloride for the elution, there being obtained dimethyl {(5-diallylamino-2-oxo-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-7-yl)imino}diacetate. Pure substance is produced by recrystallization from diisopropyl ether; melting point 93°-95° C.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue is dissolved in methylene chloride
  3. extractionwater and then extracted twice with methylene chloride
  4. dry with materialThe combined organic extracts are dried over potassium carbonate
  5. customevaporated under reduced pressure
  6. customThe residue is chromatographed over silica gel using a 0.5% mixture of methanol in methylene chloride
  7. washfor the elution, there

Sources & evidence

ORD record
ord-a059731f33b24c848307505eeb46c015
Source dataset
uspto-grants-1982_06
Patent number
US04336380

Reaction notes

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