Dibutyltin oxide → HCID 178431717, compound

HRID 1278662Notes

Reaction equation

HRID 1278662 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) δ10.4 (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-5dc85cf6d81a473b8dc8c28912c26562
Source dataset
uspto-grants-2002_09
Patent number
US06444668B1

Reaction notes

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