Water → HCID 58972969, compound

HRID 1171067Notes

Reaction equation

HRID 1171067 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[C:3]=1[C:4]#[N:5].O.C(Cl)Cl.CO>CCO>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[C:3]=1[CH2:4][NH2:5]

Participants

5

Reactant 3

HCID 962WaterHCID 21226129Dichloromethane methanolHCID 68770387HCID 68770387, compound

Product 1

HCID 58972969HCID 58972969, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2-fluoro-6-[1,2,4]triazol-1-yl-benzonitrile (1.54 g, 8.20 mmol), as prepared in the previous step, in dry EtOH (70 mL) was bubbled with NH3 gas for 5 min. This solution was treated with a suspension of Raney Nickel 2800 in EtOH under air (15 mL) (prepared by diluting 2 mL of the Aldrich water slurry with 15 mL EtOH, centrifuging, decanting, diluting with 15 mL EtOH and transferring to the reaction). The flask was then sealed and evacuated until bubbles formed, and the evacuated flask was flushed with H2 gas via balloon pressure. After 14 h stirring at rt under balloon H2 pressure, TLC demonstrated very little starting material remaining. The bulk of the Raney nickel was removed with a magnet, the reaction mixture was filtered (0.22 μm), and the clear pale yellow filtrate was concentrated to give a green oil. Silica flash chromatography of the crude oil (40 mm×6″ column; 98:2 DCM/MeOH/saturated NH3 eluent; 30 mL fractions; fractions 12-19 combined) afforded the title compound as a yellow solid (1.41 g, 89%).

Workup

  1. customwas bubbled with NH3 gas for 5 min
  2. additionThis solution was treated with a suspension of Raney Nickel 2800 in EtOH under air (15 mL) (
  3. customprepared
  4. customdecanting
  5. additiondiluting with 15 mL EtOH and transferring to the reaction)
  6. customThe flask was then sealed
  7. customevacuated until bubbles
  8. customformed
  9. customthe evacuated flask was flushed with H2 gas via balloon pressure
  10. customThe bulk of the Raney nickel was removed with a magnet
  11. filtrationthe reaction mixture was filtered (0.22 μm)
  12. concentrationthe clear pale yellow filtrate was concentrated
  13. customto give a green oil

Sources & evidence

ORD record
ord-93de0908dcd744df992f28381a757eab
Source dataset
uspto-grants-2010_11
Patent number
US07829584B2

Reaction notes

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