Propargyl bromide → HCID 20025630, compound

HRID 1723342Notes

Reaction equation

HRID 1723342 reaction equation
[SH:1][C:2]1[S:3][C:4]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)=[N:5][N:6]=1.[CH3:12][C:13](C)([O-])[CH3:14].[K+].C(Br)C#C>O1CCOCC1>[CH2:14]([S:1][C:2]1[S:3][C:4]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)=[N:5][N:6]=1)[C:13]#[CH:12]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 23665647Potassium tert-butoxideHCID 178527954HCID 178527954, compound

Product 1

HCID 20025630HCID 20025630, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6 g of 2-mercapto-5-thienyl-1,3,4-thiadiazole are placed in 40 ml of dioxan and stirred for 15 minutes with 3.36 g of potassium tert.-butoxide. Subsequently, 5.9 g of propargyl bromide are added dropwise at 30° C. and the reaction mixture is stirred overnight at room temperature. The salts are filtered off, the filtrate is concentrated by evaporation, the residue is taken up in methylene chloride and the solution is washed with water and then with 1N sodium hydroxide solution. The solvent is removed in vacuo and the residue obtained is 6.1 g of crude title compound which, recrystallised from tert.-butyl methyl ether, yields the title compound having a melting point of 71°-73° C.

Workup

  1. filtrationThe salts are filtered off
  2. concentrationthe filtrate is concentrated by evaporation
  3. washthe solution is washed with water
  4. customThe solvent is removed in vacuo
  5. customthe residue obtained
  6. customrecrystallised from tert.-butyl methyl ether

Sources & evidence

ORD record
ord-ca9716c84af14dc4916e7c0987df6102
Source dataset
uspto-grants-1989_08
Patent number
US04861787

Reaction notes

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