Dibutyltin oxide → HCID 178496911, compound

HRID 2228302Notes

Reaction equation

HRID 2228302 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:12][CH2:11][CH2:10][C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:8][C:7]=2[CH:17]=1)#[N:2].C[Si]([N:22]=[N+:23]=[N-:24])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[NH:22]1[C:1]([C:3]2[CH:4]=[CH:5][C:6]3[O:12][CH2:11][CH2:10][C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:8][C:7]=3[CH:17]=2)=[N:2][N:24]=[N:23]1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 18472647Methyl 7-cyano-2,3-dihydro-1-benzoxepine-4-carboxylate

Product 1

HCID 178496911HCID 178496911, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

In toluene (15 ml) was suspended methyl 7-cyano-2,3-dihydro-1-benzoxepine-4-carboxylate (642 mg, 2.80 mmol), and to the mixture were added trimethylsilylazide (0.929 ml, 7.00 mmol) and dibutyl tin oxide (70 mg, 0.28 mmol). The mixture was stirred at 100° C. for 24 hours and concentrated under reduced pressure. To the residue was added methanol, and the mixture was concentrated under reduced pressure. To the residue was added ethyl acetate, and the mixture was extracted with saturated sodium bicarbonate solution (30 ml, 10 ml×2). To the aqueous layer was added 6N hydrochloric acid to make the solution about pH 1, and the mixture was extracted with ethyl acetate and THF ((30 ml50 ml) and (10 ml/10 ml)×2). The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure, to the residue was added ethyl acetate. Insoluble materials were filtered, which were washed with ethyl acetate and dried under reduced pressure to give methyl 7-(1H-tetrazol-5-yl)-2,3-dihydro-1-benzoxepine-4-carboxylate (662 mg, 2.43 mmol, 87%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue was added methanol
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionTo the residue was added ethyl acetate
  5. extractionthe mixture was extracted with saturated sodium bicarbonate solution (30 ml, 10 ml×2)
  6. additionTo the aqueous layer was added 6N hydrochloric acid
  7. extractionthe mixture was extracted with ethyl acetate and THF ((30 ml50 ml) and (10 ml/10 ml)×2)
  8. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure, to the residue
  10. additionwas added ethyl acetate
  11. filtrationInsoluble materials were filtered
  12. washwhich were washed with ethyl acetate
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-36825c690506408db3155f8bd5f3274c
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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