Thionyl Chloride → 3,4-Dichloro-5-[(2-chloroethyl)sulfanyl]-1-methyl-1H-pyrazole

HRID 1632228Notes

Reaction equation

HRID 1632228 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9]O)=[C:5]([Cl:11])[C:4]([Cl:12])=[N:3]1.S(Cl)([Cl:15])=O>C(Cl)Cl.N1C=CC=CC=1.CCOCC>[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][Cl:15])=[C:5]([Cl:11])[C:4]([Cl:12])=[N:3]1

Participants

6

Reactant 2

HCID 24386Thionyl ChlorideHCID 13341318HCID 13341318, compound

Product 1

HCID 133739603,4-Dichloro-5-[(2-chloroethyl)sulfanyl]-1-methyl-1H-pyrazole

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 48.4 g (0.213 moles) 1-methyl-3,4-dichloro-5-(2-hydroxyethylthio)pyrazole and 50 ml thionyl chloride in 200 ml methylene chloride, about 1 ml pyridine was added. The reaction mixture was heated at reflux for about 12 hours over 2 days time. The solvent was stripped, and the residue was taken up in ether. The etheral solution was washed 5 times with water and then dried over magnesium sulfate. Stripping of the ether gave 52.2 g of the product as a brown-red oil.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for about 12 hours over 2 days time
  4. washThe etheral solution was washed 5 times with water
  5. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-88a26040922d40c4be3c32591fee6171
Source dataset
uspto-grants-1984_10
Patent number
US04474797

Reaction notes

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