Chlorotrimethylsilane → HCID 86732295, compound

HRID 517174Notes

Reaction equation

HRID 517174 reaction equation
C[Si](Cl)(C)C.[C:6]1(=[O:13])[CH2:11][CH2:10][CH2:9][C:8](=[O:12])[CH2:7]1.[CH:14]([C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1)=O.[F:24][C:25]([F:37])([F:36])[C:26]1[CH:27]=[C:28]([NH:32][C:33]([NH2:35])=[O:34])[CH:29]=[CH:30][CH:31]=1>CN(C)C=O.C(#N)C.O>[C:20]([C:19]1[CH:22]=[CH:23][C:16]([CH:14]([C:7]2[C:8](=[O:12])[CH2:9][CH2:10][CH2:11][C:6]=2[OH:13])[NH:35][C:33]([NH:32][C:28]2[CH:29]=[CH:30][CH:31]=[C:26]([C:25]([F:36])([F:37])[F:24])[CH:27]=2)=[O:34])=[CH:17][CH:18]=1)#[N:21]

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 104341,3-CyclohexanedioneHCID 25712(3-Trifluoromethylphenyl)ureaHCID 660424-Cyanobenzaldehyde

Product 1

HCID 86732295HCID 86732295, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Trimethylsilyl chloride (50.7 mL, 400 mmol) is added to a solution of cyclohexane-1,3-dione (11.2 g, 100 mmol), 4-formylbenzonitrile (13.8 g, 105 mmol) and 1-(3-(trifluoromethyl)phenyl)urea (20.4 g, 100 mmol) in a mixture of N,N-dimethylformamide (100 mL) and acetonitrile (150 mL), and the mixture is stirred at room temperature over night. The reaction mixture is poured into a mixture of water and ice (2 L) and stirred for 2 h. The mixture is filtered and the precipitate is dried under reduced pressure. Yield: 41.9 g; ESI mass spectrum [M+H]+=430, Retention time HPLC: 0.91 min (Z018_S04).

Workup

  1. stirringstirred for 2 h
  2. filtrationThe mixture is filtered
  3. customthe precipitate is dried under reduced pressure
  4. custom0.91 min (Z018_S04)

Sources & evidence

ORD record
ord-ccf62b5cb9a240d29488b17645e13de5
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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