Hydrochloric Acid → HCID 21094269, compound

HRID 1350083Notes

Reaction equation

HRID 1350083 reaction equation
Cl.[Cl:2][CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[CH:7]=[N:6][CH:5]=1.[C-:16]#[N:17].[K+]>C(=O)([O-])[O-].[K+].[K+].ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O.CCOCC>[ClH:2].[CH3:15][O:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH:7]=[N:6][CH:5]=[C:4]2[CH2:3][C:16]#[N:17]

Participants

9

Reactant 3

HCID 313Hydrochloric Acid2×HCID 9032Potassium CyanideHCID 23064387HCID 23064387, compound

Product 1

HCID 21094269HCID 21094269, compound

Reagents, catalysts & solvents 5

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 11430Potassium CarbonateSolvent

Procedure

The hydrochloride of the compound obtained in Step C (0.60 g; 0.0024 mol) is dissolved in 10 ml of a saturated aqueous potassium carbonate solution and 40 ml of dichloromethane. Tetrabutylammonium bromide (2 g; 0.006 mol) and potassium cyanide (0.80 g; 0.012 mol) are then added to the preceding solution. The reaction mixture is stirred at ambient temperature for 24 hours. The solution is extracted with dichloromethane, and the organic phase is washed with water, dried over magnesium sulphate, filtered and evaporated. The oil obtained is taken up in acetone and in ether saturated with HCl(g). The precipitate formed is suction-filtered off and recrystallised from toluene/cyclohexane, 5/5, to yield the title compound in the form of a yellow solid.

Workup

  1. extractionThe solution is extracted with dichloromethane
  2. washthe organic phase is washed with water
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe oil obtained
  7. customThe precipitate formed
  8. filtrationis suction-filtered off
  9. customrecrystallised from toluene/cyclohexane, 5/5

Sources & evidence

ORD record
ord-3d13e700da924f3db0e44aa227daa3d9
Source dataset
uspto-grants-2007_05
Patent number
US07214689B2

Reaction notes

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