Acetic Acid → HCID 20335700, compound

HRID 2420480Notes

Reaction equation

HRID 2420480 reaction equation
[O:1]=[C:2]1[N:6]2[C:7]3[CH:23]=[CH:22][C:21](Cl)=[N:20][C:8]=3[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])=[N+:10]([O-:12])[CH2:11][C:5]2=[N:4][NH:3]1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1.O.C(O)(=O)C>C(Cl)(Cl)Cl>[O:1]=[C:2]1[N:6]2[C:7]3[CH:23]=[CH:22][C:21]([N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[N:20][C:8]=3[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])=[N+:10]([O-:12])[CH2:11][C:5]2=[N:4][NH:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 31268PyrrolidineHCID 20335684HCID 20335684, compound

Product 1

HCID 20335700HCID 20335700, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

15 grams of 1-keto-6-(o-chlorophenyl)-8-chloro-1,2-dihydro-4H-s-triazolo-(4,3-a)-pyrido-(2,3-f)-(1,4)-diazepine-5-oxide in 50 ml. of pyrrolidine were boiled at reflux with stirring for 1 hour. Then it was poured into 600 ml. of water and neutralized with acetic acid. The precipitated material was shaken with chloroform, the chloroform layer washed with water, dried and evaporated to dryness. The residue was dissolved in methanol, acidified with ethanolic HCl solution and treated with ether up to the beginning of turbidity. The material crystallized out. It was filtered off with suction and washed with methanol-ether, and then recrystallized again from methanol-ether. Yield 4 grams; M.P. 200° C. (hydrochloride).

Workup

  1. temperatureat reflux
  2. additionThen it was poured into 600 ml
  3. washthe chloroform layer washed with water
  4. customdried
  5. customevaporated to dryness
  6. dissolutionThe residue was dissolved in methanol
  7. additiontreated with ether up to the beginning of turbidity
  8. customThe material crystallized out
  9. filtrationIt was filtered off with suction
  10. washwashed with methanol-ether
  11. customrecrystallized again from methanol-ether

Sources & evidence

ORD record
ord-53e5a02d76404f92a63a00fe1fbfb6d7
Source dataset
uspto-grants-1978_08
Patent number
US04110455

Reaction notes

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