Hydrochloric Acid → HCID 20535101, compound

HRID 1156611Notes

Reaction equation

HRID 1156611 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(N(CC)CC)C.[Cl:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1.Cl>O.C(Cl)Cl>[Cl:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([NH:1][C:2]2[N:7]3[O:8][C:9](=[O:11])[N:10]=[C:6]3[N:5]=[C:4]([N:12]([CH2:16][CH:17]=[CH2:18])[CH2:13][CH:14]=[CH2:15])[N:3]=2)=[O:32])=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 20535125HCID 20535125, compound

Product 1

HCID 20535101HCID 20535101, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

5.0 g. of 7-amino-5-diallylamino-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-2-one are suspended in 7 ml. of triethylamine and 150 ml. of methylene chloride. 3.4 ml. of 4-chlorobenzoyl chloride in 35 ml. of methylene chloride are added dropwise while stirring and cooling to about 0° C. The mixture is subsequently stirred at about 0° C. for 1 hour. Water is then added thereto and the pH is adjusted to 4 with dilute hydrochloric acid solution. The two phases are separated and the aqueous phase is extracted twice 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 pure p-chloro-N-{5-diallylamino-2-oxo-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-7-yl}benzamide having a melting point of 192°-194° C.

Workup

  1. stirringThe mixture is subsequently stirred at about 0° C. for 1 hour
  2. customThe two phases are separated
  3. extractionthe aqueous phase is extracted twice with methylene chloride
  4. dry with materialThe combined organic extracts are dried over sodium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThe residue is recrystallized from methylene chloride and diethyl ether, there

Sources & evidence

ORD record
ord-645860eca69c44189d4d77f9644dc87f
Source dataset
uspto-grants-1982_06
Patent number
US04336380

Reaction notes

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