Trimethylsilyl cyanide → HCID 86761697, compound

HRID 1880243Notes

Reaction equation

HRID 1880243 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C:13]2([C:26]([F:29])([F:28])[F:27])[O:17][N:16]=[C:15]([C:18]3[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=3)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C[Si]([C:36]#[N:37])(C)C.[NH3:38].CO>[I-].[Zn+2].[I-]>[NH2:38][CH:22]([C:21]1[CH:24]=[CH:25][C:18]([C:15]2[CH2:14][C:13]([C:5]3[CH:6]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:8]=[C:3]([C:2]([F:30])([F:1])[F:31])[CH:4]=3)([C:26]([F:28])([F:27])[F:29])[O:17][N:16]=2)=[CH:19][CH:20]=1)[C:36]#[N:37]

Participants

5

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 21705897Ammonia methanolHCID 86761695HCID 86761695, compound

Product 1

HCID 86761697HCID 86761697, compound

Reagents, catalysts & solvents 1

HCID 9883512zinc(II)iodideCatalyst

Conditions

Temperature
0 °C

Procedure

To a mixture of 0.83 g of 4-[5-[3,5-bis(trifluoromethyl)phenyl]-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzaldehyde and 0.36 g of trimethylsilylcyanide, 0.01 g of zinc iodide was added while stirring the mixture at 0° C. The resultant mixture was stirred at 60° C. for 10 minutes, and then left to be cooled down to room temperature. 2 mL of a 2M ammonia-methanol solution was added to the resultant reaction mixture, followed by continuing the stirring of the resultant reaction mixture at 50° C. further for 3.5 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:2) to obtain 0.60 g of the objective substance as a brown resinoid.

Workup

  1. additionwas added
  2. waitleft
  3. temperatureto be cooled down to room temperature
  4. customreaction mixture
  5. stirringstirring of the resultant
  6. customreaction mixture at 50° C. further for 3.5 hours
  7. customAfter the completion of the reaction
  8. distillationthe solvent was distilled off under reduced pressure
  9. customthe resultant residue was purified by silica gel column chromatography
  10. washeluting with ethyl acetate-hexane (1:2)
  11. customto obtain 0.60 g of the objective substance as a brown resinoid

Sources & evidence

ORD record
ord-0c0a74c2db7b467aaae41771da941a1b
Source dataset
uspto-grants-2012_11
Patent number
US08318757B2

Reaction notes

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