Chlorotrimethylsilane → HCID 86732301, compound

HRID 517181Notes

Reaction equation

HRID 517181 reaction equation
C[Si](Cl)(C)C.[F:6][C:7]([F:17])([F:16])[CH:8]1[CH2:13][C:12](=[O:14])[CH2:11][C:10](=[O:15])[CH2:9]1.[CH:18]([C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1)=O.[F:28][C:29]([F:41])([F:40])[C:30]1[CH:31]=[C:32]([NH:36][C:37]([NH2:39])=[O:38])[CH:33]=[CH:34][CH:35]=1>CN(C)C=O.C(#N)C.O>[C:24]([C:23]1[CH:26]=[CH:27][C:20]([CH:18]([C:11]2[C:12](=[O:14])[CH2:13][CH:8]([C:7]([F:16])([F:17])[F:6])[CH2:9][C:10]=2[OH:15])[NH:39][C:37]([NH:36][C:32]2[CH:33]=[CH:34][CH:35]=[C:30]([C:29]([F:40])([F:41])[F:28])[CH:31]=2)=[O:38])=[CH:21][CH:22]=1)#[N:25]

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 25712(3-Trifluoromethylphenyl)ureaHCID 660424-CyanobenzaldehydeHCID 592265745-(Trifluoromethyl)cyclohexane-1,3-dione

Product 1

HCID 86732301HCID 86732301, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Trimethylsilyl chloride (775 μL, 6.11 mmol) is added to a solution of 5-(trifluoromethyl)-cyclohexane-1,3-dione (1.00 g, 5.55 mmol), 4-formylbenzonitrile (728 mg, 5.55 mmol) and 1-(3-(trifluoromethyl)phenyl)urea (1.13 g, 5.55 mmol) in a mixture of N,N-dimethylform-amide (4.3 mL) and acetonitrile (8.3 mL), and the mixture is stirred at room temperature for 1 h. The reaction mixture is cooled to room temperature and poured into a mixture of water and ice. The precipitate is filtered and dried under reduced pressure. Yield: 2.38 g; ESI mass spectrum [M+H]+=498, Retention time HPLC: 0.75 min (V011_S01).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationThe precipitate is filtered
  3. customdried under reduced pressure
  4. custom0.75 min (V011_S01)

Sources & evidence

ORD record
ord-a6f55d9e05c348ba9b8f8ce6ad71943d
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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