Trimethylsilyl cyanide → HCID 13672817, compound

HRID 1732014Notes

Reaction equation

HRID 1732014 reaction equation
[CH:1]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH:7](O)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C[Si]([C:20]#[N:21])(C)C>C1C=CC=CC=1.[Zn+2].[I-].[I-]>[C:20]([CH:7]1[S:6][C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:10]=2[C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]1=2)#[N:21]

Participants

5

Reactant 2

HCID 82115Trimethylsilyl cyanideHCID 13153992HCID 13153992, compound

Product 1

HCID 13672817HCID 13672817, compound

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 241BenzeneSolvent

Procedure

6H-dibenzo[b,d]thiopyran-6-ol (2.6 g; 12 mmol) was dissolved in anhydrous benzene (50 ml). Trimethylsilylcyanide (4.5 ml; 36 mmol) and a catalytic amount of ZnI2 were added to the solution, then the reaction mixture was stirred for 20 hours at room temperature. The solution was washed with 1N NaOH, dried and evaporated. The residue was crystallized from diethyl ether to give 6-cyano-6H-dibenzo[b,d]thiopyran as white solid (2.3 g; 10 mmol); m.p. 114°-116° C. By proceeding analogously the following compounds were obtained:

Workup

  1. washThe solution was washed with 1N NaOH
  2. customdried
  3. customevaporated
  4. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-0dc182d6cfdb4b4f89c631919520c558
Source dataset
uspto-grants-1986_11
Patent number
US04624949

Reaction notes

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