Tributyltin azide → HCID 178420153, compound

HRID 257643Notes

Reaction equation

HRID 257643 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=3)[O:23][CH2:24][C:25]#[N:26])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Sn]([N:43]=[N+:44]=[N-:45])(CCCC)CCCC)CCC>C(OCC)(=O)C.Cl>[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=3)[O:23][CH2:24][C:25]3[NH:45][N:44]=[N:43][N:26]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 4984872Tributyltin azideHCID 10022670HCID 10022670, compound

Product 1

HCID 178420153HCID 178420153, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-[3-[2-(4,5-diphenyl-2-oxazolyl)ethyl]phenoxy]acetonitrile (1.60 g, 4.2 mmol) and tri-n-butyltin azide (1.45 g, 4.4 mmol) was stirred at 140° C. under an atomosphere of nitrogen. After 20 hours, the mixture was cooled, diluted with ethyl acetate (300 mL) and 1N HCl (200 mL) and the mixture stirred for 2 hours. The aqueous phase was removed and the organic phase added to 0.1M potassium fluoride solution. After stirring overnight, the organic layer was separated, washed with water and saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on a column of silica gel using a mixture of chloroform and methanol (10:1) as eluent to give 5-[[3-[2-(4,5-diphenyl-2-oxazolyl)ethyl]phenoxy]methyl]-1H-tetrazole (1.18 g, 66%) after recrystallization from a mixture of hexanes and CH2Cl2 m.p. 138.5°-140° C.

Workup

  1. temperaturethe mixture was cooled
  2. stirringthe mixture stirred for 2 hours
  3. customThe aqueous phase was removed
  4. additionthe organic phase added to 0.1M potassium fluoride solution
  5. stirringAfter stirring overnight
  6. customthe organic layer was separated
  7. washwashed with water and saturated sodium chloride solution
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was chromatographed on a column of silica gel using
  11. additiona mixture of chloroform and methanol (10:1) as eluent

Sources & evidence

ORD record
ord-5b76eac683264e43ad5673854d6c0955
Source dataset
uspto-grants-1993_11
Patent number
US05262540

Reaction notes

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