Water → 5-Chloro-3-(ethylsulfanyl)-1,2,4-thiadiazole

HRID 1392217Notes

Reaction equation

HRID 1392217 reaction equation
O.Br.C([NH:5][C:6](=[NH:8])[SH:7])C.[Cl:9][C:10]([SH:13])(Cl)Cl.[OH-].[Na+].[C:16](OC)(C)(C)[CH3:17]>>[CH2:16]([S:7][C:6]1[N:5]=[C:10]([Cl:9])[S:13][N:8]=1)[CH3:17]

Participants

6

Reactant 5

HCID 962Water2×HCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 178419564HCID 178419564, compound

Product 1

HCID 230793905-Chloro-3-(ethylsulfanyl)-1,2,4-thiadiazole

Procedure

To 60 ml of water, 10.3 g of ehtylisothiourea hydrobromide, 10.4 g of perchloromethylmercaptan were added, followed the solution of 9.39 g of sodium hydroxide dissolved to 60 ml of water was added dropwise slowly at about 0° C. Then, t-butylmethylether was added to the reaction mixture, and extracted. The organic layer was dried by anhydrous sodium salfate, and concentrated. The residue obtaind was subjected to silica gel column chromatography (hexanne:ethylacetate=30:1) to obtain 2.54 g of 3-ethylthio-5-chloro-1,2,4-thiadiazole.

Workup

  1. additionwas added dropwise slowly at about 0° C
  2. extractionextracted
  3. dry with materialThe organic layer was dried by anhydrous sodium salfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-93036e25438b436287b77393ef266a3f
Source dataset
uspto-grants-2008_03
Patent number
US07342031B2

Reaction notes

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