Ethanethiol → HCID 12889522, compound

HRID 1164318Notes

Reaction equation

HRID 1164318 reaction equation
[CH2:1]([S:5]([C:8]1[S:9][C:10](Cl)=[N:11][N:12]=1)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].[CH2:14]([SH:16])[CH3:15]>O1CCOCC1>[CH2:14]([S:16][C:10]1[S:9][C:8]([S:5]([CH2:1][CH2:2][CH2:3][CH3:4])(=[O:7])=[O:6])=[N:12][N:11]=1)[CH3:15]

Participants

4

Reactant 2

HCID 6343EthanethiolHCID 12889521HCID 12889521, compound

Product 1

HCID 12889522HCID 12889522, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

114.5 g 2-butylsulfonyl-5-chloro-1,3,4-thiadiazole and 36 ml ethylmercaptan are dissolved in 400 ml dioxane. Then under agitation 70 ml triethylamine are added to this drop by drop and the solution is heated to boiling under reflux for about one hour. After cooling the reaction mixture is introduced into ice water, the separating oil is extracted with dichloromethane, the methylenechloride phase is dried with magnesiumsulfate and the solvent is completely distilled off, finally in vacuo. 125.3 g of a colorless oil, that is 99 percent of theory, are obtained with an index of refraction of nD20 =1.5552.

Workup

  1. additionThen under agitation 70 ml triethylamine are added to this drop by drop
  2. temperaturethe solution is heated
  3. temperatureunder reflux for about one hour
  4. temperatureAfter cooling the reaction mixture
  5. extractionthe separating oil is extracted with dichloromethane
  6. dry with materialthe methylenechloride phase is dried with magnesiumsulfate
  7. distillationthe solvent is completely distilled off, finally in vacuo
  8. customare obtained with an index of refraction of nD20 =1.5552

Sources & evidence

ORD record
ord-612fd0be01074e3aa509320d3bb8262a
Source dataset
uspto-grants-1983_01
Patent number
US04369185

Reaction notes

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