Iodoethane → HCID 59457732, compound

HRID 1711102Notes

Reaction equation

HRID 1711102 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5](I)[CH3:6].[C:8]([C:10]1[S:18][C:17]2[C:12](=[N:13][CH:14]=[CH:15][C:16]=2[O:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:21]=2[F:29])[CH:11]=1)#[CH:9]>CS(C)=O.O.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH2:5]([N:1]1[CH:9]=[C:8]([C:10]2[S:18][C:17]3[C:12](=[N:13][CH:14]=[CH:15][C:16]=3[O:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:21]=3[F:29])[CH:11]=2)[N:3]=[N:2]1)[CH3:6]

Participants

7

Reactant 3

HCID 6340IodoethaneHCID 33557Sodium AzideHCID 59457702HCID 59457702, compound

Product 1

HCID 59457732HCID 59457732, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

To a solution of NaN3 (107.3 mg, 1.65 mmol) in DMSO (5 ml) was added ethyl iodide (257 mg, 1.65 mmol) and the reaction mixture was stirred for 12 hrs at RT. The alkyne 410 (520 mg, 1.65 mmol) and Cu(OAc)2×H2O (66 mg, 0.2 eq, 0.331 mmol) were added and the deep red reaction mixture was allowed to stir at RT overnight. After 72 hrs, an orange precipitate had formed. The mixture was diluted with water and the solid was collected by filtration. The orange solid 413 was used directly in the next step with no additional purification (620 mg, 97% yield). LCMS: 386.2 (M+H).

Workup

  1. customthe deep red reaction mixture
  2. stirringto stir at RT overnight
  3. waitAfter 72 hrs
  4. customan orange precipitate had formed
  5. filtrationthe solid was collected by filtration
  6. customThe orange solid 413 was used directly in the next step with no additional purification (620 mg, 97% yield)

Sources & evidence

ORD record
ord-01a847ad1a324a21822e6011800fc7be
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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