Water → 3,4-Dichloro-1-methyl-5-(propylsulfanyl)-1H-pyrazole

HRID 1632729Notes

Reaction equation

HRID 1632729 reaction equation
[CH2:1]([SH:4])[CH2:2][CH3:3].[OH-].[K+].[CH3:7][N:8]1[C:12](Cl)=[C:11]([Cl:14])[C:10]([Cl:15])=[N:9]1.O>CS(C)=O>[CH3:7][N:8]1[C:12]([S:4][CH2:1][CH2:2][CH3:3])=[C:11]([Cl:14])[C:10]([Cl:15])=[N:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 7848Propyl mercaptanHCID 14797Potassium HydroxideHCID 14751841H-Pyrazole, 3,4,5-trichloro-1-methyl-

Product 1

HCID 133743743,4-Dichloro-1-methyl-5-(propylsulfanyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A stirred mixture of 4.9 g (0.064 moles) propanthiol and 3 g (0.054 moles) potassium hydroxide in 50 ml dimethylsulfoxide was heated (at about 120° C.) for thirty minutes. Then 10 g (0.054 moles) 1-methyl-3,4,5-trichloropyrazole was added in one portion. Heating (at about 120° C.) of the stirred reaction mixture was continued for about 6 hours. The reaction mixture was allowed to cool. The reaction mixture was added to water (about 50 ml); the resulting mixture was extracted with ether. The etheral phase was separated, washed with water twice, and dried over magnesium sulfate. The solvent was then stripped. The product was distilled out at 124° C. under high vacuum and heat.

Workup

  1. temperatureHeating
  2. custom(at about 120° C.) of the stirred reaction mixture
  3. temperatureto cool
  4. extractionthe resulting mixture was extracted with ether
  5. customThe etheral phase was separated
  6. washwashed with water twice
  7. dry with materialdried over magnesium sulfate
  8. distillationThe product was distilled out at 124° C. under high vacuum
  9. temperatureheat

Sources & evidence

ORD record
ord-11451eb847714e94a1bc5d892792080c
Source dataset
uspto-grants-1984_10
Patent number
US04477462

Reaction notes

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