Ammonia → HCID 70529619, compound

HRID 2166885Notes

Reaction equation

HRID 2166885 reaction equation
N.[Na].[C:3](#[N:5])[CH3:4].[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]#[N:12]>O1CCCC1.CCOCC>[NH2:12][C:11]([C:7]1[S:6][CH:10]=[CH:9][CH:8]=1)=[CH:4][C:3]#[N:5]

Participants

7

Reactant 4

HCID 222Ammonia2×HCID 6342AcetonitrileHCID 660872-ThiophenecarbonitrileHCID 5360545Sodium2×

Product 1

HCID 70529619HCID 70529619, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

About 100 ml. of ammonia is condensed in the reaction flask and a small piece of sodium is added, giving a blue color. The color is discharged with ferric chloride and 2.7 g. of sodium is added. When the blue color disappears, 4.91 ml. of acetonitrile in 10 ml. of ether is added. The reaction is cooled in a dry ice-acetone bath and 9.28 g. of 2-thiophenecarbonitrile in 25 ml. of tetrahyrofuran is added dropwise. Cooling is continued for 30 minutes, then the ammonia and solvent are allowed to evaporate. A 50 ml. portion of water is added and the mixture is extracted with methylene chloride. The methylene chloride extracts are dried over sodium sulfate and then passed through Magnesol. Hexanes are added and the filtrate is evaporated on a steam bath to an oil. The oil is dry column chromatographed on silica gel, eluting with methylene chlorie. The fraction containing the desired product is taken up in methylene chloride, passed through Magnesol and the filtrate is evaporated on a steam bath with the addition of hexanes until an oil comes out. Cooling and seeding gives the desired product as crystals, mp. 50°-45° C.

Workup

  1. customcondensed in the reaction flask
  2. customgiving a blue color
  3. temperatureThe reaction is cooled in a dry ice-acetone bath
  4. temperatureCooling
  5. customto evaporate
  6. additionportion of water is added
  7. extractionthe mixture is extracted with methylene chloride
  8. dry with materialThe methylene chloride extracts are dried over sodium sulfate
  9. additionHexanes are added
  10. customthe filtrate is evaporated on a steam bath to an oil
  11. customThe oil is dry column
  12. customchromatographed on silica gel
  13. washeluting with methylene chlorie
  14. additionThe fraction containing the desired product
  15. customthe filtrate is evaporated on a steam bath with the addition of hexanes until an oil
  16. temperatureCooling

Sources & evidence

ORD record
ord-6f1a38835e9e4827a195648760b3c28e
Source dataset
uspto-grants-1983_06
Patent number
US04390545

Reaction notes

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