Sodium Chloride → HCID 13343349, compound

HRID 1263055Notes

Reaction equation

HRID 1263055 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][N:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:6]=2[CH:21]=1.[I:22]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+].[Cl-].[Na+]>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([I:22])=[N:13][N:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:6]=2[CH:21]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 13343348HCID 13343348, compound

Product 1

HCID 13343349HCID 13343349, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred mixture of 0.339 gm (1 mmol) of 8-bromo-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine and 25 ml of benzene was treated with 0.242 gm (1.1 mmol) of N-iodosuccinimide and refluxed under nitrogen for 12 hr and 40 min. The mixture was cooled and was then mixed with ice water containing sodium bicarbonate and sodium chloride and was finally extracted with methylene chloride. The extract was washed with dilute sodium chloride, dried with sodium sulfate and concentrated in vacuo. The residue was crystallized from methylene chloride-methanol to yield one batch of 0.252 gm, which melted with decomposition between 209° and 212.5° C. and another batch of 0.020 gm which melted with decomposition between 196° and 198.5° C. A portion of the first batch was recrystallized twice by being dissolved in almost pure methylene chloride to which methanol was slowly added during concentration. After this recrystallization, the title product melted with decomposition between 200° and 207° C. Another sample for analysis was prepared by essentially the same procedure and, after recrystallization from methylene chloride-methanol, molded with decomposition between 216° and 219° C. Analysis of the product for carbon, hydrogen and nitrogen showed C: 41.04%, H: 2.11%, N: 12.10%. Calculated values for such an analysis of the product are: C: 41.31%; H: 2.16% and N: 12.05%.

Workup

  1. temperaturerefluxed under nitrogen for 12 hr and 40 min
  2. temperatureThe mixture was cooled
  3. extractionwas finally extracted with methylene chloride
  4. washThe extract was washed with dilute sodium chloride
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized from methylene chloride-methanol
  8. customto yield one batch of 0.252 gm, which
  9. custommelted with decomposition between 209° and 212.5° C.
  10. custommelted with decomposition between 196° and 198.5° C
  11. customA portion of the first batch was recrystallized twice
  12. dissolutionby being dissolved in almost pure methylene chloride to which methanol
  13. additionwas slowly added during concentration
  14. customAfter this recrystallization
  15. custommelted with decomposition between 200° and 207° C
  16. customAnother sample for analysis was prepared by essentially the same procedure
  17. customafter recrystallization from methylene chloride-methanol
  18. custommolded with decomposition between 216° and 219° C

Sources & evidence

ORD record
ord-536c1be543c54ee1b121aa9221ce4d4e
Source dataset
uspto-grants-1984_06
Patent number
US04455307

Reaction notes

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