Hydrochloric Acid → HCID 20535093, compound

HRID 1156619Notes

Reaction equation

HRID 1156619 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](Cl)(=[O:22])[CH:20]=[CH2:21].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:19](=[O:22])[CH:20]=[CH2:21])[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 13140Acryloyl chlorideHCID 20535125HCID 20535125, compound

Product 1

HCID 20535093HCID 20535093, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

6.5 g. of 7-amino-5-diallylamino-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-2-one are suspended in 120 ml. of methylene chloride and 8 ml. of triethylamine. 3 ml. of acrylyl chloride in 35 ml. of methylene chloride are added dropwise at 0° C. while stirring. The mixture is then stirred for 2 hours, diluted with 100 ml. of water and adjusted to pH 4 with 2-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 chromatographed over silica gel using methylene chloride and methanol for the elution and the desired substance is recrystallized from methylene chloride and diethyl ether, there being obtained pure N-{5-diallylamino-2-oxo-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-7-yl}acrylamide having a melting point of 157°-161° C.

Workup

  1. stirringThe mixture is then stirred for 2 hours
  2. additiondiluted with 100 ml
  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 chromatographed over silica gel
  8. washfor the elution
  9. customthe desired substance is recrystallized from methylene chloride and diethyl ether, there

Sources & evidence

ORD record
ord-fc128774da9940c2a766ede28089fb46
Source dataset
uspto-grants-1982_06
Patent number
US04336380

Reaction notes

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