Acetonitrile → HCID 12939838, compound

HRID 2285891Notes

Reaction equation

HRID 2285891 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[C:10](#[N:12])[CH3:11].[H-].[Na+].C(O)(C)(C)C>O.CO.CCOCC>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]([CH2:11][C:10]#[N:12])=[NH:6]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 6386tert-ButanolHCID 24758Sodium hydrideHCID 678803-Fluorobenzonitrile

Product 1

HCID 12939838HCID 12939838, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A 1.21 g. portion of m-fluorobenzonitrile, 0.52 ml. of acetonitrile, 0.5 g. of sodium hydride and 0.1 ml. of t-butanol are added to 25 ml. of ether. The mixture is refluxed on a steam bath for one hour. Methanol and water are added. The layers are separated and the aqueous layer is extracted with two 25 ml. portions of ether. The combined ether layers are dried over sodium sulfate, passed through diatomaceous earth, diluted with hexanes and evaporated on a steam bath. The resulting oil is chromatographed using methylene chloride on silica gel giving 0.52 g. of an oil which crystallizes. This material is taken up in methylene chloride. Hexanes are added and the mixture is evaporated, giving an oil with crystallizes. This material is recrystallized from carbon tetrachloride giving the desired product, mp. 67°-68° C.

Workup

  1. temperatureThe mixture is refluxed on a steam bath for one hour
  2. customThe layers are separated
  3. extractionthe aqueous layer is extracted with two 25 ml
  4. dry with materialThe combined ether layers are dried over sodium sulfate
  5. additiondiluted with hexanes
  6. customevaporated on a steam bath
  7. customThe resulting oil is chromatographed
  8. customof an oil which crystallizes
  9. additionHexanes are added
  10. customthe mixture is evaporated
  11. customgiving an oil
  12. customwith crystallizes
  13. customThis material is recrystallized from carbon tetrachloride giving the desired product, mp. 67°-68° C.

Sources & evidence

ORD record
ord-73a2c3d687244d09b89eadf1e83ddc61
Source dataset
uspto-grants-1982_04
Patent number
US04325949

Reaction notes

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