Dibutyltin oxide → HCID 178517467, compound

HRID 748400Notes

Reaction equation

HRID 748400 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:12]2[N:17]=[C:16]([CH2:18][CH2:19][C:20]#[N:21])[CH:15]=[CH:14][CH:13]=2)=[N:3]1.C[Si]([N:26]=[N+:27]=[N-:28])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[NH:26]1[C:20]([CH2:19][CH2:18][C:16]2[N:17]=[C:12]([C:4]3[S:5][C:6]4[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=4[C:2](=[O:1])[N:3]=3)[CH:13]=[CH:14][CH:15]=2)=[N:21][N:28]=[N:27]1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 59750098HCID 59750098, compound

Product 1

HCID 178517467HCID 178517467, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propionitrile (0.25 g, 0.85 mmol) and trimethylsilylazide (0.20 g, 1.7 mol) were dissolved in toluene (5 ml), and dibutyltin (IV) oxide (0.02 g, 0.08 mmol) was added thereto. The reaction mixture was refluxed for 48 hrs and kept at room temperature. The precipitated crystals were collected by filtration, washed with toluene and recrystallized from ethanol to give the titled compound (0.20 g, 68%) as white crystals.

Workup

  1. temperatureThe reaction mixture was refluxed for 48 hrs
  2. customkept at room temperature
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with toluene
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a5b545814a3649d3bcd07686a3a714fb
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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