HCID 86590979, compound → HCID 18509275, compound

HRID 1356690Notes

Reaction equation

HRID 1356690 reaction equation
[F:1][B-](F)(F)F.[C:6]([C:8]1[CH:13]=[C:12]([S:14][C:15]#[N:16])[CH:11]=[CH:10][C:9]=1[N+]#N)#[N:7]>O>[F:1][C:9]1[CH:10]=[CH:11][C:12]([S:14][C:15]#[N:16])=[CH:13][C:8]=1[C:6]#[N:7]

Participants

3

Reactant 1

HCID 86590979HCID 86590979, compound

Product 1

HCID 18509275HCID 18509275, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

2-Cyano-4-(thiocyanato)benzenediazonium fluoroborate (2.98 g (10.9 mmol)) was decomposed by first heating with a heat-gun until until the whole mass became black and then by heating to 200° C. in an oil bath for 30 minutes. After cooling, water was added and the resulting mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was then distilled by means of a glass tube oven under reduced pressure, and a fraction which boiled at 180-240 ° C./0.2 mmHg was collected to give 0.29 g (15%) of 2-fluoro-5-(thiocyanato)benzonitrile as a pale yellow-white crystals.

Workup

  1. temperatureby first heating with
  2. temperaturea heat-gun until until the whole mass
  3. temperatureAfter cooling
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. distillationThe residue was then distilled by means of a glass tube oven under reduced pressure
  9. customa fraction which boiled at 180-240 ° C./0.2 mmHg was collected

Sources & evidence

ORD record
ord-28064ae61ce34206b89ec57ebc430432
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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