Ammonia → HCID 70529619, compound

HRID 1733302Notes

Reaction equation

HRID 1733302 reaction equation
[Na].[C:2](#[N:4])[CH3:3].[S:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[C:10]#[N:11].N>O1CCCC1.C(OCC)C>[NH2:11][C:10]([C:6]1[S:5][CH:9]=[CH:8][CH:7]=1)=[CH:3][C:2]#[N:4]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6342AcetonitrileHCID 660872-ThiophenecarbonitrileHCID 5360545Sodium2×

Product 1

HCID 70529619HCID 70529619, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A reaction flask is dried by flaming with a stream of nitrogen passing through it. 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 diethyl ether is added. The reaction is cooled in a dry ice-acetone bath and 9.28 g. of 2-thiophenecarbonitrile in 25 ml. of tetrahydrofuran 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. This oil is dry column chromatographed on silica gel, eluting with methylene chloride. 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, m.p. 50°-54° C.

Workup

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

Sources & evidence

ORD record
ord-f73cb8d5bb2645a494372f42a268f656
Source dataset
uspto-grants-1980_12
Patent number
US04241077

Reaction notes

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