Hydrochloric Acid → HCID 178519391, compound

HRID 489229Notes

Reaction equation

HRID 489229 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 02/26718) 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-f3588980872e4b6fb109c6b152cde53d
Source dataset
uspto-grants-2005_12
Patent number
US06977267B2

Reaction notes

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