Potassium Carbonate → HCID 178509606, compound

HRID 498944

Reaction equation

HRID 498944 reaction equation
[S:1]([C:19]1[CH:24]=[C:23]([C:25]2[C:26]([C:30]([F:33])([F:32])[F:31])=[N:27][NH:28][CH:29]=2)[CH:22]=[CH:21][C:20]=1[C:34]#[N:35])[C:2]1C=C(C2C(C(F)(F)F)=NNC=2)C=CC=1C#N.C(S([O-])=O)O.[Na+].C(=O)([O-])[O-].[K+].[K+].[F:48][C:49]([F:53])([F:52])CI>CN(C)C=O.O>[F:48][C:49]([F:53])([F:52])[CH2:2][S:1][C:19]1[CH:24]=[C:23]([C:25]2[C:26]([C:30]([F:32])([F:33])[F:31])=[N:27][NH:28][CH:29]=2)[CH:22]=[CH:21][C:20]=1[C:34]#[N:35]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 23689980Sodium Formaldehyde SulfoxylateHCID 178509604HCID 178509604, compound

Product 1

HCID 178509606HCID 178509606, compoundYield 142.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2.7 g (5.0 mmol) of 1,1′-thiodi-[2-cyano-5-(3-trifluoromethylpyrazolyl)benzene], 3.0 g (19.5 mmol) of Rongalite, 3.0 g (21.7 mmol) of potassium carbonate and 6.1 g (29.0 mmol) of 2,2,2-trifluoroethyl iodide were stirred in 50 ml of N,N-dimethylformamide at room temperature for 3 hours. The resulting reaction mixture was poured into 300 ml of water and extracted with 50 ml of ethyl acetate twice. The ethyl acetate layer was washed with 50 ml of water twice and dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 2.5 g of 2-(2,2,2-trifluoroethylthio)-4-(3-trifluoromethylpyrazolyl)benzonitrile (yield 71.4%) as a brown solid (m.p. 65-67° C.).

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with 50 ml of ethyl acetate twice
  3. washThe ethyl acetate layer was washed with 50 ml of water twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe ethyl acetate was distilled off under reduced pressure
  6. customPurification of the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-003062d3a2e549e7ac93dd195807b67a
Source dataset
uspto-grants-2010_08
Patent number
US07767626B2

Linked notes

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