Potassium Cyanide → HCID 53800255, compound

HRID 1422166Notes

Reaction equation

HRID 1422166 reaction equation
[C-:1]#[N:2].[K+].[CH:4]1([O:9][C:10]2[CH:11]=[C:12]([C:18]3[CH:19]=[N:20][C:21](S(C)(=O)=O)=[N:22][CH:23]=3)[CH:13]=[CH:14][C:15]=2[O:16][CH3:17])[CH2:8][CH2:7][CH2:6][CH2:5]1.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH:4]1([O:9][C:10]2[CH:11]=[C:12]([C:18]3[CH:19]=[N:20][C:21]([C:1]#[N:2])=[N:22][CH:23]=3)[CH:13]=[CH:14][C:15]=2[O:16][CH3:17])[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 516892Sodium BicarbonateHCID 18778862HCID 18778862, compound

Product 1

HCID 53800255HCID 53800255, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of potassium cyanide (205 mg) in dry DMF (10 ml) was added the compound of Example 12 (1.0 g) and the reaction mixture stirred at room temperature for 3 hr then at 50° C. for 2 h. The reaction mixture was poured into a saturated NaHCO3 solution (2.5 g Na2CO3 in 120 ml ice). The resulting yellow precipitate was filtered off and washed with water. Recrystallisation from EtOAc/hexane (1:2) gave the title compound (575 mg) as yellow needles (mp 121-123° C.). Found C, 69.15; H, 5.73; N, 14.13. C17H17N3O2 requires C, 69.14; H, 5.80; N, 14.23%.

Workup

  1. waitat 50° C. for 2 h
  2. filtrationThe resulting yellow precipitate was filtered off
  3. washwashed with water
  4. customRecrystallisation from EtOAc/hexane (1:2)

Sources & evidence

ORD record
ord-cdeafef8fe4a41aba0f7d1474607eb33
Source dataset
uspto-grants-2000_06
Patent number
US06080790

Reaction notes

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