Hydrochloric Acid → HCID 20535123, compound

HRID 1680927Notes

Reaction equation

HRID 1680927 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.[C:19]1([CH2:25][C:26](Cl)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>O.C(Cl)Cl.C(N(CC)CC)C>[CH2:13]([N:12]([CH2:16][CH:17]=[CH2:18])[C:4]1[N:3]=[C:2]([NH:1][C:26](=[O:27])[CH2:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:7]2[O:8][C:9](=[O:11])[N:10]=[C:6]2[N:5]=1)[CH:14]=[CH2:15]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 7679Phenylacetyl chlorideHCID 20535125HCID 20535125, compound

Product 1

HCID 20535123HCID 20535123, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

4.5 g. of 7-amino-5-diallylamino-2H-[1,2,4]-oxadiazolo[2,3-a]-s-triazin-2-one are suspended in 100 ml. of methylene chloride and 10 ml. of triethylamine. 4.8 ml. of phenylacetyl chloride in 30 ml. of methylene chloride are added dropwise while stirring and cooling. The mixture is then stirred at room temperature for 70 minutes, treated with water and adjusted to pH 4 with 3-N hydrochloric acid. The two phases are separated and the aqueous phase is extracted with methylene chloride. The combined organic extracts are dried over sodium sulfate and evaporated to dryness under reduced pressure. The residue is recrystallized from methylene chloride and diethyl ether, there being obtained N-{5-diallylamino-2-oxo-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-7-yl}-2-phenyl-acetamide having a melting point of 165°-167° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture is then stirred at room temperature for 70 minutes
  3. customThe two phases are separated
  4. extractionthe aqueous phase is extracted with methylene chloride
  5. dry with materialThe combined organic extracts are dried over sodium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customThe residue is recrystallized from methylene chloride and diethyl ether, there

Sources & evidence

ORD record
ord-38d32039d1e5488890faa40d7a845080
Source dataset
uspto-grants-1981_06
Patent number
US04276417

Reaction notes

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