1-Butyne → HCID 23288263, compound

HRID 368293Notes

Reaction equation

HRID 368293 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](Cl)=[N:10][OH:11])[CH:5]=[N:6][C:7]=1[Cl:8].C(N(CC)CC)C.[CH:20]#[C:21][CH2:22][CH3:23]>CCOCC>[Cl:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([C:9]2[CH:20]=[C:21]([CH2:22][CH3:23])[O:11][N:10]=2)=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 78461-ButyneHCID 8471TriethylamineHCID 72643028HCID 72643028, compound

Product 1

HCID 23288263HCID 23288263, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

5,6-Dichloro-N-hydroxy-3-pyridinecarboximidoyl chloride (0.85 g, 3.8 mmol) was dissolved with stirring in ether (60 mL) and a solution of triethylamine (0.8 g, 7.9 mmol) in ether (50 mL) added dropwise to the solution while 1-butyne was bubbled through the reaction mixture. The mixture was stirred at room temperature overnight, filtered, and the filtrate evaporated to dryness under reduced pressure. Recrystallisation of the residue from hexane gave the desired product (0.83 g, 90%) as a cream solid, melting point. 98-9° C.

Workup

  1. customwas bubbled through the reaction mixture
  2. filtrationfiltered
  3. customthe filtrate evaporated to dryness under reduced pressure
  4. customRecrystallisation of the residue from hexane

Sources & evidence

ORD record
ord-a77702c573d44e00a5c2f1f77cf14353
Source dataset
uspto-grants-2000_10
Patent number
US06133294

Reaction notes

Loading…