Pivaloyl chloride → N-(1H-1,2,4-triazol-3-yl)pivalamide

HRID 1157785Notes

Reaction equation

HRID 1157785 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([NH2:6])=[N:2]1.[C:7](Cl)(=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9]>C1(C)C=CC=CC=1>[NH:1]1[CH:5]=[N:4][C:3]([NH:6][C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9])=[N:2]1

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 178418311HCID 178418311, compound

Product 1

HCID 178447248N-(1H-1,2,4-triazol-3-yl)pivalamideYield 25%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 1H-1,2,4-triazol-3-amine (500 mg, 5.95 mmol) and TEA (0.829 mL, 5.95 mmol) in toluene (25 mL) was added pivaloyl chloride (0.732 mL, 5.95 mmol). The mixture was heated up at 110° C. for 13 h. The reaction mixture was quenched with water, filtered and the extracted with ethyl acetate (3×10 ml). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to afford N-(1H-1,2,4-triazol-3-yl)pivalamide (250 mg, 25%) as white solid. 1H NMR (500 MHz, MeOD) δ ppm 1.48 (s, 9H) 7.48 (s, 1H).

Workup

  1. customThe reaction mixture was quenched with water
  2. filtrationfiltered
  3. extractionthe extracted with ethyl acetate (3×10 ml)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-706b35d7da4e4b42864ae8dbe2e154f0
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

Loading…