Ethanethiol → HCID 178477362, compound

HRID 617012Notes

Reaction equation

HRID 617012 reaction equation
[CH2:1]([SH:3])[CH3:2].C([O:6][C:7]([NH:9][N:10]([CH2:13][CH3:14])[C:11]#[N:12])=O)C>C(O)(=O)C>[CH2:13]([N:10]1[C:11]([S:3][CH2:1][CH3:2])=[N:12][C:7]([OH:6])=[N:9]1)[CH3:14]

Participants

4

Reactant 2

HCID 6343EthanethiolHCID 53744342HCID 53744342, compound

Product 1

HCID 178477362HCID 178477362, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To an ethanolic solution of sodium ethylate produced from 4.6 g of sodium and 100 ml of absolute ethanol there is firstly added dropwise 14.9 g of ethyl mercaptan and subsequently 31.4 g of 2-ethyl-2-cyanohydrazinecarboxylic acid ethyl ester is added dropwise. There is formed a crystalline precipitate, which is refluxed for 3 hours. The cooled suspension is freed, after the addition of 12 g of glacial acetic acid, by filtration from the precipitated sodium acetate, and the filtrate is concentrated in vacuo to dryness. 200 ml of chloroform is added to the residue and filtration is performed. The filtrate is again concentrated to dryness. The residue is recrystallised with cyclohexane. There is obtained 26 g (75% of theory) of 1-ethyl-5-ethylthio-3-hydroxy-1,2,4-triazole, m.p. 65°-68° C.

Workup

  1. additionis added dropwise
  2. customThere is formed a crystalline precipitate, which
  3. temperatureis refluxed for 3 hours
  4. filtrationby filtration from the precipitated sodium acetate
  5. concentrationthe filtrate is concentrated in vacuo to dryness
  6. addition200 ml of chloroform is added to the residue and filtration
  7. concentrationThe filtrate is again concentrated to dryness
  8. customThe residue is recrystallised with cyclohexane

Sources & evidence

ORD record
ord-a20ba992b2004e1f8f2c2acea3bc9444
Source dataset
uspto-grants-1978_02
Patent number
US04076938

Reaction notes

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