Dimethyl Sulfoxide → HCID 53765127, compound

HRID 1447055Notes

Reaction equation

HRID 1447055 reaction equation
I[C:2]([F:11])([F:10])[C:3]([F:9])([F:8])[C:4]([F:7])([F:6])I.I[C:13]1[CH:14]=[C:15]([C:21]#[N:22])[C:16](=[CH:19][CH:20]=1)[C:17]#[N:18].CS(C)=O>[Cu].O>[C:21]([C:15]1[CH:14]=[C:13]([C:2]([F:11])([F:10])[C:3]([F:9])([F:8])[C:4]([F:7])([F:6])[C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([C:21]#[N:22])[CH:14]=2)[CH:20]=[CH:19][C:16]=1[C:17]#[N:18])#[N:22]

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 41200244-IodophthalonitrileHCID 109164621,1,2,2,3,3-Hexafluoro-1,3-diiodopropane

Product 1

HCID 53765127HCID 53765127, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

1, 3-Diiodoperfluoropropane (2.0 g, 5 mmol), 1.8 g (30 meq) of activated copper, 2.5 g (10 mmol) of 4 - iodophthalonitrile and 6 ml of dry dimethyl sulfoxide were purged for 15 minutes with argon and the mixture was then heated at 115°-120° C. for 4 hours. After cooling, the content was poured into 100 ml of water and extracted with four 50 ml portions of ether. The combined ethereal extract was washed with water, charcoaled, dried over anhydrous sodium sulfate and concentrated at reduced pressure to afford 1.1 g (52%) of product, m.p. 133°-135° C.

Workup

  1. temperaturethe mixture was then heated at 115°-120° C. for 4 hours
  2. temperatureAfter cooling
  3. extractionextracted with four 50 ml portions of ether
  4. extractionThe combined ethereal extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-c5e1d09fa4174fab821dc4f77c7d3628
Source dataset
uspto-grants-1982_02
Patent number
US04315093

Reaction notes

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