Chlorotrimethylsilane → HCID 9936243, compound

HRID 2288558Notes

Reaction equation

HRID 2288558 reaction equation
N(OC(C)(C)C)=O.C[Si]([Cl:12])(C)C.N[C:14]1[C:18]([CH:19]2[CH2:21][C:20]2([Br:23])[Br:22])=[CH:17][N:16]([C:24]2[C:29]([Cl:30])=[CH:28][C:27]([C:31]([F:34])([F:33])[F:32])=[CH:26][C:25]=2[Cl:35])[N:15]=1>ClCCl>[Cl:12][C:14]1[C:18]([CH:19]2[CH2:21][C:20]2([Br:23])[Br:22])=[CH:17][N:16]([C:24]2[C:25]([Cl:35])=[CH:26][C:27]([C:31]([F:34])([F:33])[F:32])=[CH:28][C:29]=2[Cl:30])[N:15]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 10906Tert-Butyl nitriteHCID 9913636HCID 9913636, compound

Product 1

HCID 9936243HCID 9936243, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

t-Butyl nitrite (0.07 ml) was added dropwise to a stirred solution of trimethylsilyl chloride (0.08 ml) in anhydrous dichloromethane (2.5 ml) at about -5° C. After a further 5 minutes, a solution of the title compound of Example 8 (0.10 g) in anhydrous dichloromethane (4.5ml) was added dropwise, whilst maintaining the reaction temperature below -5° C. Next, the reaction mixture was allowed to warm to room temperature, stirred for 45 minutes more and then evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, using mixtures of hexane:dichloromethane (9:1 then 4:1) as eluants, to afford the title compound as a colourless gum. δ (CDCl3): 1.85 (t,1H), 2.25 (dd,1H), 2.70 (dd,1H), 7.35 (s,1H), 7.75 (s,2H). MS (thermospray): M/Z [M+H] 510.7; C13H6Br2Cl3F3N2 +H requires 510.80.

Workup

  1. temperaturewhilst maintaining the reaction temperature below -5° C
  2. customevaporated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-970ebfcb37074694bbc0d570732a9019
Source dataset
uspto-grants-2000_07
Patent number
US06090394

Reaction notes

Loading…