Dibutyltin oxide → HCID 178517466, compound

HRID 748425Notes

Reaction equation

HRID 748425 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[CH:17]=[C:16]([CH2:18][CH2:19][C:20]#[N:21])[CH:15]=[CH:14][N: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[CH:15]=[CH:14][N:13]=[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:17]=2)=[N:21][N:28]=[N:27]1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 59750230HCID 59750230, compound

Product 1

HCID 178517466HCID 178517466, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-[2-(4-Oxo-4H-1,3-benzothiazin-2-yl)-4-pyridyl]propionitrile (0.25 g, 0.85 mmol) and trimethylsilyl azide (0.20 g, 1.7 mmol) 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 and washed with toluene. The obtained crystals were recrystallized from ethanol to give the titled compound (0.13 g, 44%) 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. customThe obtained crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-709866a0283d4a06b5b4a192886ddb2d
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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