Dichloromethane → HCID 20535104, compound

HRID 1156614Notes

Reaction equation

HRID 1156614 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(Cl)Cl.C(N(CC)CC)C.[C:29](Cl)(=[O:32])[CH2:30][CH3:31]>O>[CH2:13]([N:12]([CH2:16][CH:17]=[CH2:18])[C:4]1[N:3]=[C:2]([NH:1][C:29](=[O:32])[CH2:30][CH3:31])[N:7]2[O:8][C:9](=[O:11])[N:10]=[C:6]2[N:5]=1)[CH:14]=[CH2:15]

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 20535125HCID 20535125, compound

Product 1

HCID 20535104HCID 20535104, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5 g. of 7-amino-5-diallylamino-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-2-one are suspended in 80 ml. of methylene chloride and 5 ml. of triethylamine. 2.2 ml. of propionyl chloride in 20 ml. of methylene chloride are added dropwise at 0° C. The mixture is stirred for 90 minutes, then diluted with water, adjusted to pH 4 and extracted with methylene chloride. The combined organic extracts are dried over magnesium sulfate and evaporated under reduced pressure. The residue is chromatographed over silica gel using chloroform for the elution. Recrystallization from methylene chloride and diethyl ether yields pure N-{5-diallylamino-2-oxo-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-7-yl}propionamide having a melting point of 157°-159° C.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe combined organic extracts are dried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue is chromatographed over silica gel
  5. washfor the elution
  6. customRecrystallization from methylene chloride and diethyl ether

Sources & evidence

ORD record
ord-7c6e9ef686da479ab9fe3c260627197a
Source dataset
uspto-grants-1982_06
Patent number
US04336380

Reaction notes

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