Propargyl bromide → HCID 178460803, compound

HRID 1721263Notes

Reaction equation

HRID 1721263 reaction equation
[OH-].[K+].[NH:3]1[CH:7]=[N:6][C:5]([SH:8])=[N:4]1.[CH2:9](Br)[C:10]#[CH:11]>CO>[CH2:11]([S:8][C:5]1[N:6]=[CH:7][NH:3][N:4]=1)[C:10]#[CH:9]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 14797Potassium HydroxideHCID 178527894HCID 178527894, compound

Product 1

HCID 178460803HCID 178460803, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 21.8 g of potassium hydroxide in 400 ml of methanol under nitrogen was added 33.37 g of 1,2,4-triazole-3-thiol. The resulting mixture was stirred at ambient temperature for ~1 hour. To this mixture was added 33.4 ml of propargyl bromide dropwise while keeping the reaction temperature below 30° C. After the addition, the resulting mixture was stirred at ambient temperature for ~4 hours and was then concentrated under reduced pressure. The residue was triturated in 300 ml of water. The precipitate was collected by filtration, washed with water and then hexanes, air dried and then dried in oven to give 24.6 g of the title product as a solid, m.p. 102°-104° C. NMR (DMSO-d6): 3.14 (t, 1H); 3.92 (d, 2H); 8.48 (s, 1H); 14.2 (bs, 1H).

Workup

  1. customthe reaction temperature below 30° C
  2. additionAfter the addition
  3. stirringthe resulting mixture was stirred at ambient temperature for ~4 hours
  4. concentrationwas then concentrated under reduced pressure
  5. customThe residue was triturated in 300 ml of water
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water
  8. dry with materialhexanes, air dried
  9. customdried in oven

Sources & evidence

ORD record
ord-d483ba55142a4a0e80fbdf90410c490e
Source dataset
uspto-grants-1996_04
Patent number
US05510320

Reaction notes

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