Hydrochloric Acid → HCID 20535106, compound

HRID 1156609Notes

Reaction equation

HRID 1156609 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.[Cl:19][C:20]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23].Cl>O.C(Cl)Cl.C(N(CC)CC)C>[Cl:19][C:20]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:21]=1[C:22]([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:23]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 666452,4-Dichlorobenzoyl chlorideHCID 20535125HCID 20535125, compound

Product 1

HCID 20535106HCID 20535106, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
5 °C

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, cooled while stirring to about 5° C. and treated with 2.5 ml. of 2,4-dichlorobenzoyl chloride in 20 ml. of methylene chloride. After 1 hour at 0° C., the mixture is diluted with 100 ml. of water and adjusted to pH 4 with hydrochloric acid. 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 chromatographed over silica gel using a mixture of chloroform and methanol (99:1) for the elution. Crystallization of the residue from chloroform and diethyl ether yields 2,4-dichloro-N-{5-diallylamino-2-oxo-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-7-yl}benzamide having a melting point of 163°-164° C.

Workup

  1. additiontreated with 2.5 ml
  2. additionthe mixture is diluted with 100 ml
  3. customThe two phases are separated
  4. extractionthe aqueous phase is extracted twice 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 using
  8. additiona mixture of chloroform and methanol (99:1)
  9. washfor the elution
  10. customCrystallization of the residue from chloroform and diethyl ether

Sources & evidence

ORD record
ord-66d0f31badb3416d8f571f2755c4a8e2
Source dataset
uspto-grants-1982_06
Patent number
US04336380

Reaction notes

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