Tributyltin azide → HCID 178519099, compound

HRID 1829069Notes

Reaction equation

HRID 1829069 reaction equation
[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]([CH2:11][C:12]#[N:13])[O:3]1.[N:14]([Sn](CCCC)(CCCC)CCCC)=[N+:15]=[N-:16]>O1CCOCC1.C(Cl)(Cl)Cl.CCCCCC>[NH:14]1[C:12]([CH2:11][CH:4]2[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:2](=[O:1])[O:3]2)=[N:13][N:16]=[N:15]1

Participants

5

Reactant 2

HCID 4984872Tributyltin azideHCID 15268945(3-Oxo-1,3-dihydro-2-benzofuran-1-yl)acetonitrile

Product 1

HCID 178519099HCID 178519099, compound

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 21585165Chloroform hexaneSolvent

Procedure

A solution of (3-oxo-1,3-dihydro-2-benzofuran-1-yl)acetonitrile (890 mg, 5.14 mmol) and azidotributyltin (1.97 ml, 7.20 mmol) in dioxane (4.0 ml) was heated at 95° C. for 17 hours. The reaction was partitioned between EtOAc and saturated NaHCO3 aqueous solution, and then washed with saturated NaHCO3 aqueous solution. The aqueous layers were combined, washed with EtOAc, then acidified with 10% HCl aqueous solution. The acidic aqueous layer was extracted with EtOAc. The combined organic layers were then washed with brine, dried with anhydrous Na2SO4, and rotary evaporated to obtain a yellow oil. The oil was dissolved in CHCl3/Hexane and allowed to crystallize, leading to 3-(1 H-tetrazol-5-ylmethyl)-2-benzofuran-1(3 H)-one as a white solid (913 mg, 82%).

Workup

  1. customThe reaction was partitioned between EtOAc and saturated NaHCO3 aqueous solution
  2. washwashed with saturated NaHCO3 aqueous solution
  3. washwashed with EtOAc
  4. extractionThe acidic aqueous layer was extracted with EtOAc
  5. washThe combined organic layers were then washed with brine
  6. dry with materialdried with anhydrous Na2SO4
  7. customrotary evaporated
  8. customto obtain a yellow oil
  9. customto crystallize

Sources & evidence

ORD record
ord-bce0709a2206423db91172dbb9f20bbb
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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