Potassium Carbonate → HCID 58276234, compound

HRID 70293

Reaction equation

HRID 70293 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[CH:11][NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:13]([O-])([O-])=O.[K+].[K+].ClC[CH2:21][C:22]([CH3:27])([CH3:26])[C:23]([O-:25])=[O:24]>CC#N>[CH3:21][C:22]([CH3:27])([CH3:26])[C:23]([O:25][CH2:13][N:10]1[CH:11]=[N:12][C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)=[N:9]1)=[O:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 124615465-(3-Bromophenyl)-1H-1,2,4-triazoleHCID 217530474-Chloro-2,2-dimethylbutanoate

Product 1

HCID 58276234HCID 58276234, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A slurry of 3-(3-bromophenyl)-1H-1,2,4-triazole (58.5 g; 261 mmol; Step 1 above), anhydrous K2CO3 (43.2 g; 313 mmol), and chloromethylpivalate (45 mL; 313 mmol) in dry MeCN (250 mL) was heated to 80° C. (Note 1) for 1 hour. The mixture was cooled, solid was collected by filtration and the filtrate was concentrated in vacuo Residue from the filtaret was combined with the filtered solid and the whole was stirred with water approximately 20 minutes. Solid was collected by filtration, washed with water (×3) and recrystallized from MeOH/water, affording the title compound as a colorless solid. LC/MS (method E) tR 0.88 min, m/z 338, 340 (M+H, Br isotopes).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationsolid was collected by filtration
  3. concentrationthe filtrate was concentrated in vacuo Residue from the filtaret
  4. filtrationSolid was collected by filtration
  5. washwashed with water (×3)
  6. customrecrystallized from MeOH/water

Sources & evidence

ORD record
ord-6b23d8ffbd59492aa20d8b1a464ad044
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Linked notes

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