Ammonia → HCID 15334434, compound

HRID 962805Notes

Reaction equation

HRID 962805 reaction equation
[CH2:1]([Li])[CH2:2]CC.[Cl:6][C:7]1([C:10]([OH:20])([CH2:14][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[CH2:11][C:12]#[CH:13])[CH2:9][CH2:8]1.N.C(I)C>CCCCCC.O1CCCC1>[Cl:6][C:7]1([C:10]([OH:20])([CH2:14][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[CH2:11][C:12]#[C:13][CH2:1][CH3:2])[CH2:8][CH2:9]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6340IodoethaneHCID 15022048HCID 15022048, compoundHCID 178418339Butyllithium

Product 1

HCID 15334434HCID 15334434, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

89.7 ml (021 mol) of n-butyllithium in hexane are added at -40° C., with stirring and under a nitrogen atmosphere, to a solution of 22.5 g (0.1 mol) of 4-(1-chlorocyclopropyl)4hydroxy-5-(1,2,4-triazol-1-yl)1-pentine in 350 ml of liquid ammonia. After the end of the addition, stirring is continued initially at from -30° C. to -40° C. for 1 hour, and then a solution of 17.2 g (0.11 mol) of ethyl iodide in 20 ml of absolute tetrahydrofuran is added dropwise. The reaction mixture is subsequently stirred under ammonia reflux. For working up, the ammonia is evaporated off, ethyl acetate and water are added to the residue, and the organic phase is separated off, dried over sodium sulphate and concentrated under reduced pressure. This gives 25 g of a product which consists to the extent of 85.3% of 6-(1-chlorocyclopropyl)-6-hydroxy-7-(1,2,4-triazol-1-yl)-3-heptine. Recrystallization from ethanol gives 6-(1-chlorocyclopropyl)-6-hydroxy-7-(1,2,4triazol-1-yl)3-heptine in the form of a solid of melting point 83°-84° C. ##STR63##

Workup

  1. additionAfter the end of the addition
  2. stirringThe reaction mixture is subsequently stirred under ammonia
  3. temperaturereflux
  4. customthe ammonia is evaporated off
  5. additionethyl acetate and water are added to the residue
  6. customthe organic phase is separated off
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-adb64a6e8906498b95d1161adad53922
Source dataset
uspto-grants-1998_06
Patent number
US05760067

Reaction notes

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