Potassium ethylxanthate → Etridiazole

HRID 613973Notes

Reaction equation

HRID 613973 reaction equation
[O:1]([CH2:5][CH3:6])[C:2]([S-])=[S:3].[K+].Br[NH:9][C:10](=[NH:15])[C:11]([Cl:14])([Cl:13])[Cl:12]>O.C(Cl)Cl>[Cl:12][C:11]([Cl:14])([Cl:13])[C:10]1[N:15]=[C:2]([O:1][CH2:5][CH3:6])[S:3][N:9]=1

Participants

5

Reactant 2

HCID 2735045Potassium ethylxanthateHCID 178511853HCID 178511853, compound

Product 1

HCID 17432EtridiazoleYield 52.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

32 g (0.2 mole) of potassium ethyl xanthate was dissolved in 175 ml of water. This was stirred rapidly while a solution of 48 g (0.2 mole) of N-bromotrichloroacetamidine in 150 ml of methylene chloride was added over 15 minutes. Then, the mixture was stirred one hour at room temperature. The dark methylene chloride layer was separated and the water layer extracted with 100 ml of methylene chloride. The combined methylene chloride fractions were dried over magnesium sulfate and filtered. Next, the solvent was evaporated and then the crude product was distilled at 75° C. under a vacuum of 0.9mm to give 26 g of 3-trichloromethyl-5-ethoxy-1,2,4-thiadiazole.

Workup

  1. additionwas added over 15 minutes
  2. customThe dark methylene chloride layer was separated
  3. extractionthe water layer extracted with 100 ml of methylene chloride
  4. dry with materialThe combined methylene chloride fractions were dried over magnesium sulfate
  5. filtrationfiltered
  6. customNext, the solvent was evaporated
  7. distillationthe crude product was distilled at 75° C. under a vacuum of 0.9mm

Sources & evidence

ORD record
ord-0e81f51a02514a93ba9839b5313fe643
Source dataset
uspto-grants-1979_03
Patent number
US04143044

Reaction notes

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