Hydrochloric Acid → HCID 20535132, compound

HRID 1680929Notes

Reaction equation

HRID 1680929 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)Cl.[Cl:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:25]=1[C:26](Cl)=[O:27].Cl>O.C(N(CC)CC)C>[Cl:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:25]=1[C:26]([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)=[O:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 783922,6-Dichlorobenzoyl chlorideHCID 20535125HCID 20535125, compound

Product 1

HCID 20535132HCID 20535132, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

5.0 g. of 7-amino-5-diallylamino-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-2-one are mixed with 150 ml. of chloroform, 10 ml. of triethylamine and 4.5 ml. of 2,6-dichlorobenzoyl chloride and heated to reflux for 7 hours. The mixture is then cooled, diluted with water, adjusted to pH 4 with hydrochloric acid and extracted with chloroform. The combined organic extracts are dried over sodium sulfate and evaporated to dryness under reduced pressure. The residue is chromatographed over silica gel using a mixture of methylene chloride and methanol (99:1) for the elution. Recrystallization from diisopropyl ether and methylene chloride yields pure 2,6-dichloro-N-{5-diallylamino-2-oxo-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-7-yl}benzamide having a melting point of 133°-135° C.

Workup

  1. temperatureto reflux for 7 hours
  2. temperatureThe mixture is then cooled
  3. extractionextracted with chloroform
  4. dry with materialThe combined organic extracts are dried over sodium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThe residue is chromatographed over silica gel using
  7. additiona mixture of methylene chloride and methanol (99:1)
  8. washfor the elution
  9. customRecrystallization from diisopropyl ether and methylene chloride

Sources & evidence

ORD record
ord-65b49f1d7b9a488b9a0237b18248f526
Source dataset
uspto-grants-1981_06
Patent number
US04276417

Reaction notes

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