2-Mercaptoethanol → HCID 13341318, compound

HRID 544504Notes

Reaction equation

HRID 544504 reaction equation
[SH:1][CH2:2][CH2:3][OH:4].[OH-].[K+].[CH3:7][N:8]1[C:12](Cl)=[C:11]([Cl:14])[C:10]([Cl:15])=[N:9]1>C1OCCOCCOCCOCCOCCOC1.CS(C)=O.O>[CH3:7][N:8]1[C:12]([S:1][CH2:2][CH2:3][OH:4])=[C:11]([Cl:14])[C:10]([Cl:15])=[N:9]1

Participants

7

Reactant 3

HCID 15672-MercaptoethanolHCID 14797Potassium HydroxideHCID 14751841H-Pyrazole, 3,4,5-trichloro-1-methyl-

Product 1

HCID 13341318HCID 13341318, compoundYield 38.1%

Reagents, catalysts & solvents 3

HCID 2855718-Crown-6CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

To a mixture of 26.5 g (0.34 moles) 2-mercaptoethanol, 19 g of 85% potassium hydroxide, and a few drops of 18-Crown-6 in 250 ml of DMSO, 60 g(0.32 moles) 1-methyl-3,4,5-trichloro pyrazole (product of Example 1 or 1A)were added in portions. When the addition was complete, the reaction mixture was heated to 140° C. for 1 day. The cooled reaction mixture was diluted with water and extracted with ether. The oganic phase was washed four times with 200 ml water per time, dried and stripped. The crude product was chromatographed on a silica gel column. The product, 1-methyl-3,4-dichloro-5-(2-hydroxyethyl) thio pyrazole, was eluted from the column with ethyl acetate, yielding 27.7 g (37.7% yield) of a yellow oil.

Workup

  1. addition1A)were added in portions
  2. additionWhen the addition
  3. customThe cooled reaction mixture
  4. extractionextracted with ether
  5. washThe oganic phase was washed four times with 200 ml water per time
  6. customdried
  7. customThe crude product was chromatographed on a silica gel column
  8. washThe product, 1-methyl-3,4-dichloro-5-(2-hydroxyethyl) thio pyrazole, was eluted from the column with ethyl acetate

Sources & evidence

ORD record
ord-fc654e7391d84b03a495bd43d9d35517
Source dataset
uspto-grants-1984_05
Patent number
US04450278

Reaction notes

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