Pivaloyl chloride → HCID 2818790, compound

HRID 429808Notes

Reaction equation

HRID 429808 reaction equation
[CH3:1][N:2]1[C:6]([NH2:7])=[CH:5][C:4]([CH3:8])=[N:3]1.[C:9](Cl)(=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11]>N1C=CC=CC=1>[CH3:1][N:2]1[C:6]([NH:7][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:5][C:4]([CH3:8])=[N:3]1

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 5207211,3-Dimethyl-1H-pyrazol-5-amine

Product 1

HCID 2818790HCID 2818790, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
23 °C

Procedure

To 15.0 g (131 mmol) N-(2,5-dimethyl-2H-pyrazol-3-yl)-amine in 150 mL pyridine at 0° C. was added 19.3 mL (18.9 g, 158 mmol) of pivaloyl chloride. After stirring at 23° C. for 3.5 hours, the reaction solvent was evaporated, and the residue was evaporated with 2×200 mL toluene. The remaining solid was dissolved in 500 mL EtOAc/200 nmL H2O and extracted. The aqueous layer was extracted with 2×100 mL EtOAc, and the combined organics were washed with 1×200 mL brine, dried over MgSO4, filtered and evaporated to an orange solid. Recrystallization from hot hexanes/EtOAc gave 24.45 g (125 mmol, a 96% yield) of the title compound as an off-white, crystalline solid: mp: 86-88° C.; 1H NMR (300 MHz, CDCl3): δ1.32 (s, 9H), 2.22 (s, 3H), 3.63 (s, 3H). 5.98 (s, 1H), 7.12 (brs, 1H); IR (KBr, cm−1): 3316s, 3274s, 2967m, 2935m, 1673s, 1655m, 1570s, 1514m, 1492m, 1457m; MS (ES) m/z (relative intensity): (196, M+, 100). Anal. Calcd. for C10H17N3O: C, 61.51; H, 8.77; N, 21.52. Found: C, 61.33; H, 8.80; N, 21.23.

Workup

  1. customthe reaction solvent was evaporated
  2. customthe residue was evaporated with 2×200 mL toluene
  3. dissolutionThe remaining solid was dissolved in 500 mL EtOAc/200 nmL H2O
  4. extractionextracted
  5. extractionThe aqueous layer was extracted with 2×100 mL EtOAc
  6. washthe combined organics were washed with 1×200 mL brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated to an orange solid
  10. customRecrystallization from hot hexanes/EtOAc
  11. customgave 24.45 g (125 mmol

Sources & evidence

ORD record
ord-9cfb7586fde347cf9fd1a78157a3097d
Source dataset
uspto-grants-2001_11
Patent number
US06319941B1

Reaction notes

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