Potassium Iodide → HCID 13505772, compound

HRID 464252Notes

Reaction equation

HRID 464252 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14](=[O:15])[N:13]2[C:8]([CH2:9][O:10][C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=32)=[N:7]1.[I-].[K+].[C:22]1([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O>[C:22]1([N:28]2[CH2:33][CH2:32][N:31]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:14](=[O:15])[N:13]4[C:8]([CH2:9][O:10][C:11]5[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=54)=[N:7]3)[CH2:30][CH2:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 70961-PhenylpiperazineHCID 13505775HCID 13505775, compound

Product 1

HCID 13505772HCID 13505772, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-(4-chlorobutyl)-2,4-dihydro-1H-[1,2,4]triazolo[3,4-c][1,4]benzoxazin-1-one (see example 4, part 1), (1.40 g.; 0.005 mole), potassium iodide (0.83 g.; 0.005 mole) and N-phenylpiperazine (1.79 g.; 0.011 mole) was stirred at 100° C. for 5 hours. The reaction mixture was cooled, poured into water and extracted with methylene chloride. The methylene chloride extracts were combined, washed with dilute brine solution, dried over sodium sulfate and concentrated in vacuo. The resulting residue was chromatographed through 125 g. of silica gel, using a 2% v/v diethylamine in ethyl acetate as eluting liquid. The eluted product thus obtained, titled above, was crystallized in the manner described in example 1, hereinabove, from an ethyl acetate/Skellysolve®B hexane mixture to give 1.56 g., m.p. 89°-90° C. and 0.115 g., m.p. 85°-87° C. of the named, titled compound hereinabove. The analytical sample had melting point 89°-90.5° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with methylene chloride
  3. washwashed with dilute brine solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was chromatographed through 125 g
  7. washas eluting liquid
  8. customThe eluted product thus obtained
  9. customwas crystallized in the manner
  10. customto give 1.56 g

Sources & evidence

ORD record
ord-68f019b803f44c259f9b1139aaacce9a
Source dataset
uspto-grants-1985_10
Patent number
US04547499

Reaction notes

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