Potassium Cyanide → HCID 58392215, compound

HRID 561539Notes

Reaction equation

HRID 561539 reaction equation
[C-:1]#[N:2].[K+].CS(O[CH2:9][CH2:10][CH:11]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:12]1[C:20]2[C:15](=[C:16]([CH2:21][S:22][CH3:23])[CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)(=O)=O>CN(C=O)C>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([CH:11]([C:12]2[C:20]3[C:15](=[C:16]([CH2:21][S:22][CH3:23])[CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH2:10][CH2:9][C:1]#[N:2])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 58392110HCID 58392110, compound

Product 1

HCID 58392215HCID 58392215, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2.12 g (32.5 mmol) of potassium cyanide were added to 6.90 g (16.3 mmol) of the compound from Example 52A in 345 ml of DMF. The mixture was stirred at 80° C. for 4 h and then concentrated, and the residue was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient). 5.05 g (87% of theory) of the target compound were obtained.

Workup

  1. concentrationconcentrated
  2. washwashed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient)
  7. custom5.05 g (87% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-36118f25db2f4fac86f6e485347d05c7
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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