Hydrochloric Acid → HCID 178519391, compound

HRID 1792864Notes

Reaction equation

HRID 1792864 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH:5]([C:7]1[S:11][CH:10]=[C:9]([C:12]#[N:13])[CH:8]=1)=[O:6].O.Cl>CN(C=O)C>[NH:1]1[C:12]([C:9]2[CH:8]=[C:7]([CH:5]=[O:6])[S:11][CH:10]=2)=[N:13][N:3]=[N:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 33557Sodium AzideHCID 122800095-formylthiophene-3-carbonitrile

Product 1

HCID 178519391HCID 178519391, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium azide (2.9 g, 44.6 mmol) and TEA hydrochloride (4.13 g, 30 mmol) were added to a solution of 5-formyl-thiophene-3-carbonitrile (2 g, 15 mmol, prepared according to Intern. application WO 02126718) in DMF (50 ml). The solution was refluxed for 12 h. After cooling to RT, water was added and the solution was carefully acidified with HCl. The solution was extracted 3 times with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to yield the desired product as a brown solid (540 mg) which was used without further purification.

Workup

  1. temperatureThe solution was refluxed for 12 h
  2. extractionThe solution was extracted 3 times with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d213834817a045fc9c40e9442c732d6e
Source dataset
uspto-grants-2006_07
Patent number
US07078420B2

Reaction notes

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