Cyanogen Bromide → HCID 58045867, compound

HRID 657855Notes

Reaction equation

HRID 657855 reaction equation
[N:1]1([C:6]2[N:11]=[N:10][C:9]([NH:12][NH2:13])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.C([O-])(=O)C.[Na+].[N:19]#[C:20]Br.[OH-].[Na+]>C(O)(=O)C.O>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]3[N:10]([C:20]([NH2:19])=[N:13][N:12]=3)[N:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 10476Cyanogen BromideHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 303132375792-76-6

Product 1

HCID 58045867HCID 58045867, compoundYield 11.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

(6-Imidazol-1-ylpyridazin-3-yl)hydrazine (500 mg) were initially charged in a mixture of acetic acid (4 ml) and water (8 ml) with addition of sodium acetate (232 mg) at RT while stirring. Thereafter, the mixture was cooled to 0° C. and cyanogen bromide (330 mg) was introduced in portions. After stirring for 2.5 h, the mixture was left to stand overnight. After cooling to 0° C., the mixture was alkalized with 10 M sodium hydroxide solution and extracted repeatedly with EA. The combined EA phases were dried over sodium sulfate, filtered and concentrated. 66 mg of the title compound were isolated.

Workup

  1. stirringAfter stirring for 2.5 h
  2. waitthe mixture was left
  3. temperatureAfter cooling to 0° C.
  4. extractionextracted repeatedly with EA
  5. dry with materialThe combined EA phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5a036a86ac02487da2fa37c559008312
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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