Hydrochloric Acid → HCID 69591059, compound

HRID 1745893Notes

Reaction equation

HRID 1745893 reaction equation
Br[C:2]1([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH2:6][CH:5]=[C:4](Br)[S:3]1.[Cu](C#N)[C:14]#[N:15].Cl.[CH3:19][N:20](C=O)C>>[C:14]([C:2]1([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH2:6][CH:5]=[C:4]([C:19]#[N:20])[S:3]1)#[N:15]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 68578598HCID 68578598, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 69591059HCID 69591059, compound

Procedure

The compound (1) prepared in Preparative Example 1 and 11.8 g (0.13 mmol) of copper cyanide (CuCN) were added to a reactor containing 150 mL of DMF. The mixture was refluxed for 4 hours. After the reaction was completed, a mixture of ferric chloride (FeCl3), concentrated hydrochloric acid and distilled water (48 g: 12 mL: 72 mL) was added to the reactor and heated at 60–70° C. for 30 minutes to crush the complex compound (RCN-Cu complex). The hot solution was extracted with toluene, and the obtained organic layer was washed with 50% hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure to prepare 1.67 g of the title compound as a solid.

Workup

  1. additionwere added to a reactor
  2. temperatureThe mixture was refluxed for 4 hours
  3. distillationdistilled water (48 g: 12 mL: 72 mL)
  4. additionwas added to the reactor
  5. temperatureheated at 60–70° C. for 30 minutes
  6. customto crush the complex compound (RCN-Cu complex)
  7. extractionThe hot solution was extracted with toluene
  8. washthe obtained organic layer was washed with 50% hydrochloric acid
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. distillationdistilled under reduced pressure
  12. customto prepare 1.67 g of the title compound as a solid

Sources & evidence

ORD record
ord-928e0758af9a4d3ea15e996db389fd90
Source dataset
uspto-grants-2006_03
Patent number
US07019327B2

Reaction notes

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