Iodine → HCID 15753779, compound

HRID 1885298Notes

Reaction equation

HRID 1885298 reaction equation
[Al].II.[CH2:4](Br)[C:5]#[CH:6].[Cl:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH:12]=[CH:11][C:10]=1[C:23](=[O:30])[CH2:24][N:25]1[CH:29]=[N:28][CH:27]=[N:26]1.[Cl-].[NH4+]>O1CCCC1.[Hg]Cl>[Cl:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=2)[CH:12]=[CH:11][C:10]=1[C:23]([OH:30])([CH2:24][N:25]1[CH:29]=[N:28][CH:27]=[N:26]1)[CH2:6][C:5]#[CH:4]

Participants

8

Reactant 5

HCID 807IodineHCID 7842Propargyl bromideHCID 25517Ammonium ChlorideHCID 5359268AluminumHCID 157537781-[2-Chloro-4-(4-chlorophenoxy)phenyl]-2-(1H-1,2,4-triazol-1-yl)ethanone

Product 1

HCID 15753779HCID 15753779, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 24182Mercurous ChlorideCatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

1.05 g (39 mmol) of aluminum flakes, a spatula tipful of mercury chloride and an iodine crystal are warmed at 40° C. for one hour in 5 ml of absolute tetrahydrofuran under a nitrogen atmosphere. The mixture is heated to 60° C. and 6.9 g (58 mmol) of propargyl bromide in 10 ml of absolute tetrahydrofuran are added dropwise. The mixture is subsequently stirred at 60° C. for 60 minutes and then cooled to -60° C. A solution of 10 g (29 mmol) of 1-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-2-(1,2,4-triazol-1-yl)-ethan-1-one in 20 ml of absolute tetrahydrofuran is then added dropwise and the mixture is subsequently allowed to react first for 1 hour at 0° C. and then for 2 hours at room temperature. 20 ml of a saturated aqueous ammonium chloride solution are added, the precipitate obtained is filtered off with suction, and the filtrate is concentrated under reduced pressure. The residue is taken up in ethyl acetate, and the resulting solution is washed with water, dried over sodium sulphate and concentrated under reduced pressure. In this manner, 8.8 g (80% of theory) of 4-(2-chloro-4-(4-chlorophenoxy)-phenyl)-5-(1,2,4-triazol-1-yl)-pent-1-yn-4-ol are obtained in the form of a solid of melting point 124° C.

Workup

  1. temperaturecooled to -60° C
  2. customto react first for 1 hour at 0° C.
  3. waitfor 2 hours at room temperature
  4. customthe precipitate obtained
  5. filtrationis filtered off with suction
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. washthe resulting solution is washed with water
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f3e652b6f1b945bbb540f10b6548fe07
Source dataset
uspto-grants-1992_09
Patent number
US05143932

Reaction notes

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