Methyl chloroacetate → HCID 20535107, compound

HRID 1156620Notes

Reaction equation

HRID 1156620 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(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:24][O:23][C:21](=[O:22])[CH2:20][NH: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

Participants

5

Reactant 3

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

Product 1

HCID 20535107HCID 20535107, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3.0 g. of 7-amino-5-diallylamino-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-2-one are dissolved in 100 ml. of acetone and treated with 4 ml. of methyl chloroacetate and 4 g. of potassium carbonate. The mixture is vigorously stirred for 21 hours and then evaporated to dryness under reduced pressure. The residue is dissolved in methylene chloride and water and extracted twice with methylene chloride. The combined organic extracts are dried over potassium carbonate and evaporated under reduced pressure. The crude product is chromatographed over silica gel using a mixture of methylene chloride and methanol (99:1) for the elution, there being obtained pure N-{5-diallylamino-2-oxo-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-7-yl}glycine methyl ester which is recrystallized from acetone and petroleum ether; melting point 173°-174° C.

Workup

  1. customevaporated to dryness under reduced pressure
  2. dissolutionThe residue is dissolved in methylene chloride
  3. extractionwater and extracted twice with methylene chloride
  4. dry with materialThe combined organic extracts are dried over potassium carbonate
  5. customevaporated under reduced pressure
  6. customThe crude product is chromatographed over silica gel using
  7. additiona mixture of methylene chloride and methanol (99:1)
  8. washfor the elution, there

Sources & evidence

ORD record
ord-c16b9839c34e4522bab359a18aff220a
Source dataset
uspto-grants-1982_06
Patent number
US04336380

Reaction notes

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