Dibutyltin oxide → HCID 178505094, compound

HRID 890727Notes

Reaction equation

HRID 890727 reaction equation
C[Si]([N:5]=[N+:6]=[N-:7])(C)C.C([Sn](=O)CCCC)CCC.[C:18]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:31]/[CH:32]=[CH:33]/[C:34]1[CH:39]=[C:38]([Cl:40])[CH:37]=[C:36]([Cl:41])[CH:35]=1)[S:27]([CH3:30])(=[O:29])=[O:28])#[N:19]>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:41][C:36]1[CH:35]=[C:34](/[CH:33]=[CH:32]/[CH2:31][N:26]([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C:18]2[NH:19][N:7]=[N:6][N:5]=2)[S:27]([CH3:30])(=[O:29])=[O:28])[CH:39]=[C:38]([Cl:40])[CH:37]=1

Participants

6

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 22246898HCID 22246898, compound

Product 1

HCID 178505094HCID 178505094, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Trimethylsilylazide (0.136 mL, 1.026 mmol) and dibutyltinoxide (38 mg, 0.15 mmol) were added to a solution of trans-N-(6-cyano-hexyl)-N-[3-(3,5-dichloro-phenyl)-allyl]-methanesulfonamide (59A) (199 mg, 0.52 mmol) in toluene (4 mL). The reaction was heated at reflux overnight. The reaction was diluted with CH2Cl2 and the organic solution was washed sequentially with HCl (1N, 1×), water (1×), and brine (1×). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The product was purified via radial chromatography (CH2Cl2 to 5% MeOH/CH2Cl2) to afford the title compound (120 mg). 1H NMR (CDCl3 400 MHz) δ 7.26 (m, 3H), 6.50 (d, 1H), 6.22 (m, 1H), 4.00 (m, 2H), 3.23 (t, 2H), 3.02 (t, 2H), 2.90 (s, 3H), 1.83 (t, 2H), 1.62 (t, 2H), 1.38 (m, 4H); MS 132 (M+).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. washthe organic solution was washed sequentially with HCl (1N, 1×), water (1×), and brine (1×)
  4. dry with materialThe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was purified via radial chromatography (CH2Cl2 to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-9b3ee3b01c9d45ee9cb4fd2b18825a23
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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