Propargyl bromide → HCID 87836339, compound

HRID 277405Notes

Reaction equation

HRID 277405 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[C:6]([Cl:9])[CH:5]=[C:4]([F:10])[C:3]=1[N:11]1[C:15](=[O:16])[N:14]([CH2:17][CH2:18][CH2:19][F:20])[N:13]=[N:12]1.[CH2:21](Br)[C:22]#[CH:23].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH2:1][C:2]1[C:7]([O:8][CH2:23][C:22]#[CH:21])=[C:6]([Cl:9])[CH:5]=[C:4]([F:10])[C:3]=1[N:11]1[C:15](=[O:16])[N:14]([CH2:17][CH2:18][CH2:19][F:20])[N:13]=[N:12]1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 135854273HCID 135854273, compound

Product 1

HCID 87836339HCID 87836339, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The mixture of 1-(2-amino-4-chloro-6-fluoro-3-hydroxyphenyl)(3-fluoropropyl)-tetrazolinone (0.28 g), propargyl bromide (0.13 g), and potassium carbonate (0.14 g) in acetonitrile (5 ml) was heated under reflux for 0.5 hour. The solvent and excess reagent were removed under reduced pressure. The residue was purified by a silica gel column, eluted with ethyl acetate to give the desired product (0.33 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 0.5 hour
  3. customThe solvent and excess reagent were removed under reduced pressure
  4. customThe residue was purified by a silica gel column
  5. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-12cde158cebc41cebd6af9fc59fdc53a
Source dataset
uspto-grants-2002_03
Patent number
US06355799B1

Reaction notes

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