Sulfuryl chloride → 5-t-Butyl-4-chloro-3-propionylaminopyrazole

HRID 2164504Notes

Reaction equation

HRID 2164504 reaction equation
[C:1]([C:5]1[NH:9][N:8]=[C:7]([NH:10][C:11](=[O:14])[CH2:12][CH3:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:18])(=O)=O>C(Cl)(Cl)Cl>[C:1]([C:5]1[NH:9][N:8]=[C:7]([NH:10][C:11](=[O:14])[CH2:12][CH3:13])[C:6]=1[Cl:18])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 13235938N-(5-tert-Butyl-1H-pyrazol-3-yl)propanamide

Product 1

HCID 132359475-t-Butyl-4-chloro-3-propionylaminopyrazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5.8 g (0.03 mole) of 5-t-butyl-3-propionylaminopyrazole prepared in Example 5 was dispersed in 30 ml of chloroform, and the dispersion was stirred while adding dropwise thereto sulfuryl chloride. The mixture was further heated under reflux conditions for one hour, and the solvent was distilled off. To the residue was added a sodium bicarbonate aqueous solution whereby crystals were precipitated. The crystals were collected by filtration, washed with water and then dried to obtain 3.9 g of 5-t-butyl-4-chloro-3-propionylaminopyrazole. This product was recrystallized from hydrous methanol and found to have a melting point of 136° to 137° C.

Workup

  1. additionwhile adding dropwise
  2. temperatureThe mixture was further heated under reflux conditions for one hour
  3. distillationthe solvent was distilled off
  4. additionTo the residue was added a sodium bicarbonate aqueous solution whereby crystals
  5. customwere precipitated
  6. filtrationThe crystals were collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-654a43e769e34dd6a1d9dae1ac83719c
Source dataset
uspto-grants-1985_03
Patent number
US04505739

Reaction notes

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