2,6-Lutidine → HCID 58501886, compound

HRID 2097680Notes

Reaction equation

HRID 2097680 reaction equation
[S:1]([N:11]=[N+:12]=[N-:13])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]#[CH:22].N1C(C)=CC=CC=1C>C(Cl)(Cl)Cl.[Cu]I>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[N:13]=[N:12][N:11]([S:1]([C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=2)(=[O:2])=[O:3])[CH:22]=1

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 13661p-Toluenesulfonyl azideHCID 5859951-Chloro-2-ethynylbenzene

Product 1

HCID 58501886HCID 58501886, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tosyl azide (16) (1.0 equiv) in CHCl3 (0.5M) cooled to 0° C. was treated with 2-chlorophenyl acetylene (15) (1.2 equiv), 2,6-lutidine (1.2 equiv) and CuI (0.1 equiv). The resulting mixture was stirred at 0° C. for 24 h, quenched with 10% HCl, the layers separated and the aqueous one washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography (Hexane/AcOEt 5:1, 3:1 and 1:1) to provide 4-(2-chlorophenyl)-1-tosyl-1H-1,2,3-triazole (17) as a pale yellow crystalline solid.

Workup

  1. customquenched with 10% HCl
  2. customthe layers separated
  3. washthe aqueous one washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (Hexane/AcOEt 5:1, 3:1 and 1:1)

Sources & evidence

ORD record
ord-d5a93e2ddb9d4ef2a10b2c218bd21036
Source dataset
uspto-grants-2013_05
Patent number
US08450350B2

Reaction notes

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