Propargyl bromide → HCID 87836339, compound

HRID 1265355Notes

Reaction equation

HRID 1265355 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)-4-(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-89fbe15b1e4043e6a7c62103389b813e
Source dataset
uspto-grants-2003_04
Patent number
US06545161B2

Reaction notes

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