Dibutyltin oxide → HCID 178431717, compound

HRID 1725041Notes

Reaction equation

HRID 1725041 reaction equation
[CH3:1][C:2]1([CH3:21])[O:7][C:6](=[O:8])[NH:5][C:4]2[CH:9]=[CH:10][C:11]([C:13]3[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=3)[C:16]#[N:17])=[CH:12][C:3]1=2.C[Si]([N:26]=[N+:27]=[N-:28])(C)C.C([Sn](=O)CCCC)CCC>O1CCOCC1>[CH3:1][C:2]1([CH3:21])[O:7][C:6](=[O:8])[NH:5][C:4]2[CH:9]=[CH:10][C:11]([C:13]3[CH:20]=[CH:19][CH:18]=[C:15]([C:16]4[NH:28][N:27]=[N:26][N:17]=4)[CH:14]=3)=[CH:12][C:3]1=2

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 98142163-(4,4-Dimethyl-2-oxo-2,4-dihydro-1H-benzo[D][1,3]oxazin-6-YL)benzonitrile

Product 1

HCID 178431717HCID 178431717, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)benzonitrile (0.77 g, 2.8 mmol), trimethylsilyl azide (0.68 g, 5.6 mmol), and dibutyl tin oxide (0.071 g, 0.28 mmol) in dioxane (20 mL) was heated at reflux under a blanket of nitrogen. Upon completion of the reaction, the dioxane was removed, the organics taken up in ethyl acetate (100 mL), and washed with NaHCO3 (100 mL). The aqueous layer was acidified with 1 N aqueous HCl and extracted with ethyl acetate (100 mL). The organic layer was dried over MgSO4, and concentrated. Crystallization from ether (20 mL) gave 4,4-dimethyl-6-[3-(1H-tetrazol-5-yl)-phenyl]-1,4-dihydrobenzo[d][1,3]-oxazin-2-one as a light yellow solid (0.23 g, 26%): mp 238-240° C.; 1H-NMR (DMSO-d6) δ 10.4 (s, 1H), 8.3 (bs, 1H), 8.02 (d, 1H, J=7.66 Hz), 7.9 (d, 1H, J=7.91 Hz), 7.72-7.65 (m, 3H), 7.03 (d, 1H, J=8.75 Hz), 1.70 (s, 6H); MS (ESI) m/z 320 ([M−H]−, 100%); Anal. Calc. For C17H15N5O2: C, 63.54; H, 4.71; N, 21.79. Found: C, 62.16; H, 4.67; N, 21.31.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a blanket of nitrogen
  3. customUpon completion of the reaction
  4. customthe dioxane was removed
  5. washwashed with NaHCO3 (100 mL)
  6. extractionextracted with ethyl acetate (100 mL)
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated
  9. customCrystallization from ether (20 mL)

Sources & evidence

ORD record
ord-36c84faacf6c42f1b5d6ed2cdd0ba4f2
Source dataset
uspto-grants-2009_02
Patent number
US07488822B2

Reaction notes

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