Chlorotrimethylsilane → HCID 18671355, compound

HRID 1057292Notes

Reaction equation

HRID 1057292 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([NH:6][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[Li]CCCC.[CH3:20][Si:21](Cl)([CH3:23])[CH3:22]>CCCCCC>[Br:1][C:2]1[CH:14]=[CH:13][C:5]([N:6]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[Si:21]([CH3:23])([CH3:22])[CH3:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 145456884-Bromo-N-cyclohexylanilineHCID 178418339Butyllithium

Product 1

HCID 18671355HCID 18671355, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

9 g 4-bromo-N-cyclohexylaniline (VII) (CA registration number [113388-04-8], see Synthetic Communications, 1986, 16(13): 1641-1645 for its preparation) was placed into a four-necked flask and 15 ml (1.5 mol/L) n-BuLi solution in n-hexane. The mixture was stirred for 30 min at room temperature. Then 8 g trimethylsilyl chloride (Me3SiCl) was added and the mixture was stirred for 1 hour. Solvent and excessive Me3SiCl was evaporated under reduced to yield 4-bromo-N-cyclohexyl-N-trimethylsilylaniline) (VIII) which was formulated into a solution with 7.5 ml anhydrous tetrahydrofuran for further use.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. customSolvent and excessive Me3SiCl was evaporated

Sources & evidence

ORD record
ord-9cea3106b457497ca9077535a5d4c925
Source dataset
uspto-grants-2003_02
Patent number
US06514956B1

Reaction notes

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