Potassium Cyanide → 9H-Thioxanthene-9-carbonitrile

HRID 726765Notes

Reaction equation

HRID 726765 reaction equation
Cl([O-])(=O)(=O)=O.[CH:6]1[C:19]2[C:10](=[S+:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]=[CH:8][CH:7]=1.[C-:20]#[N:21].[K+]>O.C(Cl)Cl>[C:20]([CH:18]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:11][C:10]2[C:19]1=[CH:6][CH:7]=[CH:8][CH:9]=2)#[N:21]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 22077311Thioxanthylium perchlorate

Product 1

HCID 123928179H-Thioxanthene-9-carbonitrileYield 91.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

8.0 g (27.0 mmol) of thioxanthylium perchlorate [C. C. Price et al, J. Amer. Chem. Soc. 85, 2278 (1963)] are added to a well-stiffed mixture of 3.5 g (53.8 mmol) of potassium cyanide in 4 ml of water and 30 ml of methylene chloride under a nitrogen atmosphere. After one hour, the mixture is dried over potassium carbonate and filtered and the flitrate is concentrated on a vacuum rotary evaporator. Crystallization of the residue from isopropanol gives 5.5 g (91%) of 9-cyano-thioxanthene, melting point 103°-105° C., colourless needles (compound (103), Table I).

Workup

  1. dry with materialthe mixture is dried over potassium carbonate
  2. filtrationfiltered
  3. concentrationthe flitrate is concentrated on a vacuum rotary evaporator
  4. customCrystallization of the residue from isopropanol

Sources & evidence

ORD record
ord-7fbd8eb536f2447189b194124f94c5cf
Source dataset
uspto-grants-1998_01
Patent number
US05710198

Reaction notes

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