Propargyl bromide → HCID 18326243, compound

HRID 1250435Notes

Reaction equation

HRID 1250435 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([C:9]2[C:13]([CH3:14])=[C:12]([C:15]#[N:16])[N:11]([CH3:17])[N:10]=2)=[C:4]([F:18])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[C:26]#[CH:27]>CC(C)=O>[Cl:1][C:2]1[C:7]([O:8][CH2:27][C:26]#[CH:25])=[CH:6][C:5]([C:9]2[C:13]([CH3:14])=[C:12]([C:15]#[N:16])[N:11]([CH3:17])[N:10]=2)=[C:4]([F:18])[CH:3]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 18326234HCID 18326234, compound

Product 1

HCID 18326243HCID 18326243, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
22 °C

Procedure

1.33 g of 3-(4-chloro-2-fluoro-5-hydroxyphenyl)-4-methyl-5-cyano-1-methyl-[1H]-pyrazole (Example H6) are dissolved in 25 ml of acetone, and 1.38 g of potassium carbonate are added. The reaction mixture is stirred for 10 minutes at 22° C., and 0.89 g (0.56 ml) of propargyl bromide is then added dropwise with stirring, and stirring is continued for 5 hours at this temperature. The solvent is subsequently distilled off in vacuo and the residue is taken up in diethyl ether. After the etheric solution has been washed with water and saline and the solvent evaporated off, the desired product is obtained in a yield of 1.36 g (89.9% of theory).

Workup

  1. stirringwith stirring
  2. stirringstirring
  3. waitis continued for 5 hours at this temperature
  4. distillationThe solvent is subsequently distilled off in vacuo
  5. washAfter the etheric solution has been washed with water and saline
  6. customthe solvent evaporated off

Sources & evidence

ORD record
ord-b8332673ce9d45a68fd059d5d5d9d7bb
Source dataset
uspto-grants-2002_01
Patent number
US06339046B1

Reaction notes

Loading…