Potassium Cyanide → HCID 15428880, compound

HRID 1739605Notes

Reaction equation

HRID 1739605 reaction equation
N[C:2]1[CH:17]=[CH:16][C:5]2[S:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9](=[O:11])[CH2:10][C:4]=2[CH:3]=1.N([O-])=O.[Na+].[C-]#N.[K+].[C:25]([Cu])#[N:26]>Cl.O.CCOC(C)=O>[C:25]([C:2]1[CH:17]=[CH:16][C:5]2[S:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9](=[O:11])[CH2:10][C:4]=2[CH:3]=1)#[N:26]

Participants

8

Reactant 4

HCID 9032Potassium CyanideHCID 827053HCID 827053, compoundHCID 23668193Sodium NitriteHCID 178418546HCID 178418546, compound

Product 1

HCID 15428880HCID 15428880, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 2-amino-10-oxo-dibenzo[b,f]thiepine (1 g, 4.40 mmol) in 2 N HCl (7.00 mL) at 0° C., was slowly added a solution of NaNO2 (0.316 g, 4.60 mmol) in water (4.00 mL). A CuCN solution was prepared by heating KCN (1.30 g, 20.0 mmol) in water (5.0 mL) and adding CuSO4.5H2O (1.09 g, 4.40 mmol) solution in water (4.0 mL). Once cooled to room temperature the CuCN solution was slowly added to the diazonium salt mixture and heated to 50° C. for 1 hour. The reaction mixture was diluted with EtOAc and filtered through celite pad. The filtrate was washed with brine, dried (MgSO4) and concentrated to give an oil. The crude material was chromatographed (5%EtOAc/Hexane); yield 0.16 g (15%).

Workup

  1. filtrationfiltered through celite pad
  2. washThe filtrate was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give an oil
  6. customThe crude material was chromatographed (5%EtOAc/Hexane)

Sources & evidence

ORD record
ord-8941cffc20534eb09f795952d8739f5c
Source dataset
uspto-grants-1999_10
Patent number
US05968478

Reaction notes

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